Composition of matter for use in organic light-emitting diodes

ABSTRACT

The present disclosure relates to compounds of Formula (I) as useful materials for OLED&#39;s. At least two of Z 1 , Z 2 , Z 3 , Z 4  and Z 5  are CN, cyanoaryl, or heteroaryl having at least one nitrogen atom as a ring-constituting atom; and at least two of R 1 , R 2 , R 3  and R 4  are diarylamino, indolyl or carbazolyl.

RELATED APPLICATIONS

This application claims the benefit of priority to U.S. ProvisionalPatent Application Ser. No. 62/743,228, filed Oct. 9, 2018, which ishereby expressly incorporated by reference, in its entirety, into thepresent application.

BACKGROUND

An organic light emitting diode (OLED) is a light-emitting diode (LED)in which a film of organic compounds is placed between two conductors,which film emits light in response to excitation, such as an electriccurrent. OLEDs are useful in displays, such as television screens,computer monitors, mobile phones, and tablets. A problem inherent inOLED displays is the limited lifetime of the organic compounds. OLEDswhich emit blue light, in particular, degrade at a significantlyincreased rate as compared to green or red OLEDs.

OLED materials rely on the radiative decay of molecular excited states(excitons) generated by recombination of electrons and holes in a hosttransport material. The nature of excitation results in interactionsbetween electrons and holes that split the excited states into brightsinglets (with a total spin of 0) and dark triplets (with a total spinof 1). Since the recombination of electrons and holes affords astatistical mixture of four spin states (one singlet and three tripletsublevels), conventional OLEDs have a maximum theoretical efficiency of25%.

To date, OLED material design has focused on harvesting the remainingenergy from the normally dark triplets. Recent work to create efficientphosphors, which emit light from the normally dark triplet state, haveresulted in green and red OLEDs. Other colors, such as blue, however,require higher energy excited states which accelerate the degradationprocess of the OLED.

The fundamental limiting factor to the triplet-singlet transition rateis a value of the parameter |H_(fi)/Δ|², where H_(fi) is the couplingenergy due to hyperfine or spin-orbit interactions, and Δ is theenergetic splitting between singlet and triplet states. Traditionalphosphorescent OLEDs rely on the mixing of singlet and triplet statesdue to spin-orbital (SO) interaction, increasing H_(fj), and affording alowest emissive state shared between a heavy metal atom and an organicligand. This results in energy harvesting from all higher singlet andtriplet states, followed by phosphorescence (relatively short-livedemission from the excited triplet). The shortened triplet lifetimereduces triplet exciton annihilation by charges and other excitons.Recent work by others suggests that the limit to the performance ofphosphorescent materials has been reached.

SUMMARY

The present disclosure relates to novel materials for OLEDs. These OLEDscan reach higher excitation states without rapid degradation. It has nowbeen discovered that thermally activated delayed fluorescence (TADF),which relies on minimization of Δ as opposed to maximization of H_(fi),can transfer population between singlet levels and triplet sublevels ina relevant timescale, such as, for example, 1-100 μs. The compoundsdescribed herein are capable of luminescing at higher energy excitationstates than compounds previously described.

In one aspect, the present disclosure provides:

[1] A compound of Formula (I).

wherein:two of Z¹, Z², Z³, Z⁴ and Z⁵ are independently A,the other remaining three of Z¹, Z², Z³, Z⁴ and Z⁵ are independentlyselected from H, deuterium, substituted or unsubstituted alkyl, and A,

-   -   A is selected from CN, substituted or unsubstituted aryl having        at least one cyano, and substituted or unsubstituted heteroaryl        having at least one nitrogen atom as a ring-constituting atom,        two of R¹, R², R³ and R⁴ are independently D,        the other remaining two of R¹, R², R³ and R⁴ are selected from        H, deuterium, substituted or unsubstituted alkyl, substituted or        unsubstituted aryl, substituted or unsubstituted heteroaryl, and        D,    -   D is group of Formula (IIa), (IIb), (IIc), or (IId):

-   -   R^(D) is independently selected from hydrogen, deuterium,        substituted or unsubstituted alkyl, substituted or unsubstituted        alkoxy, substituted or unsubstituted amino, substituted or        unsubstituted aryl, substituted or unsubstituted aryloxy,        substituted or unsubstituted heteroaryl, substituted or        unsubstituted heteroaryloxy, and silyl; two or more instances of        R^(D) taken together can form a ring system;    -   R^(D′) is independently selected from hydrogen, deuterium,        substituted or unsubstituted alkyl, substituted or unsubstituted        amino, substituted or unsubstituted aryl, and substituted or        unsubstituted heteroaryl; two or more instances of R^(D′) and        R^(D) taken together can form a ring system;    -   L^(D) is independently selected from single bond, substituted or        unsubstituted arylene, and substituted or unsubstituted        heteroarylene; wherein each instance of arylene and        heteroarylene can be substituted with one or more substituents        independently selected from deuterium, substituted or        unsubstituted alkyl, substituted or unsubstituted aryl, and        substituted or unsubstituted heteroaryl; two or more of these        substituents taken together can form a ring system;    -   C—R^(D) of the benzene rings in Formulae (IIa), (IIb), (IIc) and        (IId) may be substituted with N; and    -   each “*” represents a point of attachment to Formula (I).

[2] The compound of [1], wherein two of Z¹, Z², Z³, Z⁴ and Z⁵ are CN.

[3] The compound of [1] or [2], wherein Z¹ and Z² are A.

[4] The compound of [1] or [2], wherein Z² and Z³ are A.

[5] The compound of any one of [1] to [4], wherein the other remainingthree of Z¹, Z², Z³, Z⁴ and Z⁵ are H.

[6] The compound of any one of [1] to [5], wherein two of R¹, R², R³ andR⁴ are independently group of Formula (IIa).

[7] The compound of any one of [1] to [5], wherein two of R¹, R², R³ andR⁴ are independently group of Formula (IIb).

[8] The compound of any one of [1] to [7], wherein at least one of theother remaining two of R¹, R², R³ and R⁴ is substituted or unsubstitutedaryl.

[9] The compound of any one of [1] to [7], wherein at least one of theother remaining two of R¹, R², R³ and R⁴ is unsubstituted phenyl.

[10] The compound of any one of [1] to [7], wherein three of R¹, R², R³,and R⁴ are independently D, and the remaining one of R¹, R², R³ and R⁴is H, substituted or unsubstituted alkyl, substituted or unsubstitutedaryl, or substituted or unsubstituted heteroaryl.

[11] The compound of any one of [1] to [7], wherein R¹, R², R³ and R⁴are independently D.

[12] The compound of any one of [1] to [11], wherein both of R¹ and R⁴are not H.

[13] Use of the compound of any one of [1] to [12] as a light-emittingmaterial.

[14] Use of the compound of any one of [1] to [12] as an assistantdopant.

[15] A compound of Formula (IIIa):

wherein:X is halogen,D¹, D², D³ and D⁴ are independently D,

-   -   D is a group of Formula (IIa), (IIb), (IIc) or (IId):

-   -   R^(D) is independently selected from hydrogen, deuterium,        substituted or unsubstituted alkyl, substituted or unsubstituted        alkoxy, substituted or unsubstituted amino, substituted or        unsubstituted aryl, substituted or unsubstituted aryloxy,        substituted or unsubstituted heteroaryl, substituted or        unsubstituted heteroaryloxy, and silyl; two or more instances of        R^(D) taken together can form a ring system;    -   R^(D′) is independently selected from hydrogen, deuterium,        substituted or unsubstituted alkyl, substituted or unsubstituted        amino, substituted or unsubstituted aryl, and substituted or        unsubstituted heteroaryl; two or more instances of R^(D′) and        R^(D) taken together can form a ring system;    -   L^(D) is independently selected from single bond, substituted or        unsubstituted arylene, and substituted or unsubstituted        heteroarylene; wherein each instance of arylene and        heteroarylene can be substituted with one or more substituents        independently selected from deuterium, substituted or        unsubstituted alkyl, substituted or unsubstituted aryl, and        substituted or unsubstituted heteroaryl; two or more of these        substituents taken together can form a ring system;    -   C—R^(D) of the benzene rings in Formulae (IIa), (IIb), (IIc) and        (IId) may be substituted with N; and    -   each “*” represents a point of attachment to Formula (I).

[16] The compound of [15], wherein D¹, D², D³ and D⁴ are the same.

[17] An organic light-emitting diode (OLED) comprising the compound ofany one of [1] to [12].

[18] The organic light-emitting diode (OLED) of [17], comprising ananode, a cathode, and at least one organic layer comprising alight-emitting layer between the anode and the cathode, wherein thelight-emitting layer comprises a host material and the compound.

[19] The organic light-emitting diode (OLED) of [17], comprising ananode, a cathode, and at least one organic layer comprising alight-emitting layer between the anode and the cathode, wherein thelight-emitting layer comprises the compound and a light-emittingmaterial, and light emission of the OLED occurs mainly in thelight-emitting material.

[20] The organic light-emitting diode (OLED) of [17], comprising ananode, a cathode, and at least one organic layer comprising alight-emitting layer between the anode and the cathode, wherein thelight-emitting layer comprises a host material, an assistant dopant anda light-emitting material, and the assistant dopant is the compound.

BRIEF DESCRIPTION OF THE DRAWING

FIG. 1 is a schematic wherein 1 denotes a substrate, 2 denotes an anode,3 denotes a hole injection layer, 4 denotes a hole transporting layer, 5denotes a light-emitting layer, 6 denotes an electron transportinglayer, and 7 denotes a cathode.

FIG. 2 is a time resolved spectrum of the thin film of Example 3.

DETAILED DESCRIPTION

The examples are provided by way of explanation of the disclosure, andnot by way of limitation of the disclosure. In fact, it will be apparentto those skilled in the art that various modification and variations canbe made in the present disclosure without departing from the scope orspirit of the disclosure. For instance, features illustrated ordescribed as part of one embodiment can be used on another embodiment toyield a still further embodiment. Thus, it is intended that the presentdisclosure cover such modifications and variations as come within thescope of the appended claims and their equivalents. Other objects,features, and aspects of the present disclosure are disclosed in, or canbe derived from, the following detailed description. It is to beunderstood by one of ordinary skill in the art that the presentdiscussion is a description of exemplary embodiments only, and is not tobe construed as limiting the broader aspects of the present disclosure.

Definitions

Unless otherwise defined herein, scientific and technical terms used inthis application shall have the meanings that are commonly understood bythose of ordinary skill in the art. Generally, nomenclature used inconnection with, and techniques of, chemistry described herein, arethose well-known and commonly used in the art.

The term “acyl” is art-recognized and refers to a group represented bythe general formula hydrocarbylC(O)—, preferably alkylC(O)—.

The term “acylamino” is art-recognized and refers to an amino groupsubstituted with an acyl group and may be represented, for example, bythe formula hydrocarbylC(O)NH—.

The term “acyloxy” is art-recognized and refers to a group representedby the general formula hydrocarbylC(O)O—, preferably alkylC(O)O—.

The term “alkoxy” refers to an alkyl group, having an oxygen attachedthereto. In some embodiments, an alkoxy has 1-20 carbon atoms. In someembodiments, an alkoxy has 1-12 carbon atoms. Representative alkoxygroups include methoxy, trifluoromethoxy, ethoxy, propoxy, tert-butoxyand the like.

The term “alkoxyalkyl” refers to an alkyl group substituted with analkoxy group and may be represented by the general formula alkyl-O-alkyl

The term “alkenyl”, as used herein, refers to an aliphatic groupcomprising at least one double bond and is intended to include both“unsubstituted alkenyls” and “substituted alkenyls”, the latter of whichrefers to alkenyl moieties having substituents replacing a hydrogen onone or more carbons of the alkenyl group. Typically, a straight chainedor branched alkenyl group has from 1 to about 20 carbon atoms,preferably from 1 to about 12 unless otherwise defined. Suchsubstituents may occur on one or more carbons that are included or notincluded in one or more double bonds. Moreover, such substituentsinclude all those contemplated for alkyl groups, as discussed below,except where stability is prohibitive. For example, substitution ofalkenyl groups by one or more alkyl, carbocyclyl, aryl, heterocyclyl, orheteroaryl groups is contemplated.

An “alkyl” group or “alkane” is a straight chained or branchednon-aromatic hydrocarbon which is completely saturated. Typically, astraight chained or branched alkyl group has from 1 to about 20 carbonatoms, preferably from 1 to about 12 unless otherwise defined. In someembodiments, the alkyl group has from 1 to 8 carbon atoms, from 1 to 6carbon atoms, from 1 to 4 carbon atoms, or from 1 to 3 carbon atoms.Examples of straight chained and branched alkyl groups include methyl,ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, tert-butyl, pentyl,hexyl, pentyl and octyl.

Moreover, the term “alkyl” as used throughout the specification,examples, and claims is intended to include both “unsubstituted alkyls”and “substituted alkyls”, the latter of which refers to alkyl moietieshaving substituents replacing a hydrogen on one or more substitutablecarbons of the hydrocarbon backbone. Such substituents, if not otherwisespecified, can include, for example, a halogen (e.g., fluoro), ahydroxyl, a carbonyl (such as a carboxyl, an alkoxycarbonyl, a formyl,or an acyl), a thiocarbonyl (such as a thioester, a thioacetate, or athioformate), an alkoxy, a phosphoryl, a phosphate, a phosphonate, aphosphinate, an amino, an amido, an amidine, an imine, a cyano, a nitro,an azido, a sulfhydryl, an alkylthio, a sulfate, a sulfonate, asulfamoyl, a sulfonamido, a sulfonyl, a heterocyclyl, an aralkyl, or anaromatic or heteroaromatic moiety. In preferred embodiments, thesubstituents on substituted alkyls are selected from C₁₋₆ alkyl, C₃₋₆cycloalkyl, halogen, carbonyl, cyano, or hydroxyl. In more preferredembodiments, the substituents on substituted alkyls are selected fromfluoro, carbonyl, cyano, or hydroxyl. It will be understood by thoseskilled in the art that the moieties substituted on the hydrocarbonchain can themselves be substituted, if appropriate. For instance, thesubstituents of a substituted alkyl may include substituted andunsubstituted forms of amino, azido, imino, amido, phosphoryl (includingphosphonate and phosphinate), sulfonyl (including sulfate, sulfonamido,sulfamoyl and sulfonate), and silyl groups, as well as ethers,alkylthios, carbonyls (including ketones, aldehydes, carboxylates, andesters), —CF₃, —CN and the like. Exemplary substituted alkyls aredescribed below. Cycloalkyls can be further substituted with alkyls,alkenyls, alkoxys, alkylthios, aminoalkyls, carbonyl-substituted alkyls,—CF₃, —CN, and the like.

The term “C_(x-y)” when used in conjunction with a chemical moiety, suchas, acyl, acyloxy, alkyl, alkenyl, alkynyl, or alkoxy is meant toinclude groups that contain from x to y carbons in the chain. Forexample, the term “C_(x-y) alkyl” refers to substituted or unsubstitutedsaturated hydrocarbon groups, including straight-chain alkyl andbranched-chain alkyl groups that contain from x to y carbons in thechain, including haloalkyl groups. Preferred haloalkyl groups includetrifluoromethyl, difluoromethyl, 2,2,2-trifluoroethyl, andpentafluoroethyl. C₀ alkyl indicates a hydrogen where the group is in aterminal position, a bond if internal. The terms “C_(2-y) alkenyl” and“C_(2-y) alkynyl” refer to substituted or unsubstituted unsaturatedaliphatic groups analogous in length and possible substitution to thealkyls described above, but that contain at least one double or triplebond respectively.

The term “alkylamino”, as used herein, refers to an amino groupsubstituted with at least one alkyl group.

The term “alkylthio”, as used herein, refers to a thiol groupsubstituted with an alkyl group and may be represented by the generalformula alkylS—.

The term “arylthio”, as used herein, refers to a thiol group substitutedwith an alkyl group and may be represented by the general formulaarylS—.

The term “alkynyl”, as used herein, refers to an aliphatic groupcomprising at least one triple bond and is intended to include both“unsubstituted alkynyls” and “substituted alkynyls”, the latter of whichrefers to alkynyl moieties having substituents replacing a hydrogen onone or more carbons of the alkynyl group. Typically, a straight chainedor branched alkynyl group has from 1 to about 20 carbon atoms,preferably from 1 to about 10 unless otherwise defined. Suchsubstituents may occur on one or more carbons that are included or notincluded in one or more triple bonds. Moreover, such substituentsinclude all those contemplated for alkyl groups, as discussed above,except where stability is prohibitive. For example, substitution ofalkynyl groups by one or more alkyl, carbocyclyl, aryl, heterocyclyl, orheteroaryl groups is contemplated.

The term “amide”, as used herein, refers to a group

wherein each R^(A) independently represents a hydrogen or hydrocarbylgroup, or two R^(A) are taken together with the N atom to which they areattached complete a heterocycle having from 4 to 8 atoms in the ringstructure.

The terms “amine” and “amino” are art-recognized and refer to bothunsubstituted and substituted amines and salts thereof, e.g., a moietythat can be represented by

wherein each R^(A) independently represents a hydrogen or a hydrocarbylgroup, or two R^(A) are taken together with the N atom to which they areattached complete a heterocycle having from 4 to 8 atoms in the ringstructure.

The term “aminoalkyl”, as used herein, refers to an alkyl groupsubstituted with an amino group.

The term “aralkyl”, as used herein, refers to an alkyl group substitutedwith an aryl group.

The term “aryl” as used herein include substituted or unsubstitutedsingle-ring aromatic groups in which each atom of the ring is carbon.Preferably the ring is a 6- or 20-membered ring, more preferably a6-membered ring. Preferably aryl having 6-40 carbon atoms, morepreferably having 6-25 carbon atoms.

The term “aryl” also includes polycyclic ring systems having two or morecyclic rings in which two or more carbons are common to two adjoiningrings wherein at least one of the rings is aromatic, e.g., the othercyclic rings can be cycloalkyls, cycloalkenyls, cycloalkynyls, aryls,heteroaryls, and/or heterocyclyls. Aryl groups include benzene,naphthalene, phenanthrene, phenol, aniline, and the like.

The term “carbamate” is art-recognized and refers to a group

wherein each R^(A) independently represent hydrogen or a hydrocarbylgroup, such as an alkyl group, or both R^(A) taken together with theintervening atom(s) complete a heterocycle having from 4 to 8 atoms inthe ring structure.

The terms “carbocycle”, and “carbocyclic”, as used herein, refers to asaturated or unsaturated ring in which each atom of the ring is carbon.Preferably, a carbocylic group has from 3 to 20 carbon atoms. The termcarbocycle includes both aromatic carbocycles and non-aromaticcarbocycles. Non-aromatic carbocycles include both cycloalkane rings, inwhich all carbon atoms are saturated, and cycloalkene rings, whichcontain at least one double bond. “Carbocycle” includes 5-7 memberedmonocyclic and 8-12 membered bicyclic rings. Each ring of a bicycliccarbocycle may be selected from saturated, unsaturated and aromaticrings. Carbocycle includes bicyclic molecules in which one, two or threeor more atoms are shared between the two rings. The term “fusedcarbocycle” refers to a bicyclic carbocycle in which each of the ringsshares two adjacent atoms with the other ring. Each ring of a fusedcarbocycle may be selected from saturated, unsaturated and aromaticrings. In an exemplary embodiment, an aromatic ring, e.g., phenyl (Ph),may be fused to a saturated or unsaturated ring, e.g., cyclohexane,cyclopentane, or cyclohexene. Any combination of saturated, unsaturatedand aromatic bicyclic rings, as valence permits, is included in thedefinition of carbocyclic. Exemplary “carbocycles” include cyclopentane,cyclohexane, bicyclo[2.2.1]heptane, 1,5-cyclooctadiene,1,2,3,4-tetrahydronaphthalene, bicyclo[4.2.0]oct-3-ene, naphthalene andadamantane. Exemplary fused carbocycles include decalin, naphthalene,1,2,3,4-tetrahydronaphthalene, bicyclo[4.2.0]octane,4,5,6,7-tetrahydro-1H-indene and bicyclo[4.1.0]hept-3-ene. “Carbocycles”may be substituted at any one or more positions capable of bearing ahydrogen atom.

A “cycloalkyl” group is a cyclic hydrocarbon which is completelysaturated. “Cycloalkyl” includes monocyclic and bicyclic rings.Preferably, a cycloalkyl group has from 3 to 20 carbon atoms. Typically,a monocyclic cycloalkyl group has from 3 to about 10 carbon atoms, moretypically 3 to 8 carbon atoms unless otherwise defined. The second ringof a bicyclic cycloalkyl may be selected from saturated, unsaturated andaromatic rings. Cycloalkyl includes bicyclic molecules in which one, twoor three or more atoms are shared between the two rings. The term “fusedcycloalkyl” refers to a bicyclic cycloalkyl in which each of the ringsshares two adjacent atoms with the other ring. The second ring of afused bicyclic cycloalkyl may be selected from saturated, unsaturatedand aromatic rings. A “cycloalkenyl” group is a cyclic hydrocarboncomprising one or more double bonds.

The term “carbocyclylalkyl,” as used herein, refers to an alkyl groupsubstituted with a carbocycle group.

The term “carbonate,” as used herein, refers to a group —OCO₂—R^(A),wherein R^(A) represents a hydrocarbyl group.

The term “carboxy,” as used herein, refers to a group represented by theformula —CO₂H.

The term “ester,” as used herein, refers to a group —C(O)OR^(A) whereinR^(A) represents a hydrocarbyl group.

The term “ether,” as used herein, refers to a hydrocarbyl group linkedthrough an oxygen to another hydrocarbyl group. Accordingly, an ethersubstituent of a hydrocarbyl group may be hydrocarbyl-O—. Ethers may beeither symmetrical or unsymmetrical. Examples of ethers include, but arenot limited to, heterocycle-O-heterocycle and aryl-O-heterocycle. Ethersinclude “alkoxyalkyl” groups, which may be represented by the generalformula alkyl-O-alkyl.

The terms “halo” and “halogen” as used herein means halogen and includeschloro, fluoro, bromo, and iodo.

The terms “hetaralkyl” and “heteroaralkyl,” as used herein, refers to analkyl group substituted with a hetaryl group.

The term “heteroalkyl,” as used herein, refers to a saturated orunsaturated chain of carbon atoms and at least one heteroatom, whereinno two heteroatoms are adjacent. The terms “heteroaryl” and “hetaryl”include substituted or unsubstituted aromatic single ring structures,preferably 5- to 20-membered rings, more preferably 5- to 6-memberedrings, whose ring structures include at least one heteroatom, preferablyone to four heteroatoms, more preferably one or two heteroatoms.Preferably a heteroaryl having 2-40 carbon atoms, more preferably having2-25 carbon atoms. The terms “heteroaryl” and “hetaryl” also includepolycyclic ring systems having two or more cyclic rings in which two ormore carbons are common to two adjoining rings wherein at least one ofthe rings is heteroaromatic, e.g., the other cyclic rings can becycloalkyls, cycloalkenyls, cycloalkynyls, aryls, heteroaryls, and/orheterocyclyls. Heteroaryl groups include, for example, pyrrole, furan,thiophene, imidazole, oxazole, thiazole, pyrazole, pyridine, pyrazine,pyridazine, pyrimidine, and carbazole, and the like.

The term “aryloxy” refers to an aryl group, having an oxygen attachedthereto. Preferably aryloxy having 6-40 carbon atoms, more preferablyhaving 6-25 carbon atoms.

The term “heteroaryloxy” refers to an aryl group, having an oxygenattached thereto. Preferably heteroaryloxy having 3-40 carbon atoms,more preferably having 3-25 carbon atoms.

The term “heteroatom” as used herein means an atom of any element otherthan carbon or hydrogen. Preferred heteroatoms are nitrogen, oxygen, andsulfur.

The terms “heterocyclyl,” “heterocycle,” and “heterocyclic” refer tosubstituted or unsubstituted non-aromatic ring structures, preferably 3-to 20-membered rings, more preferably 3- to 7-membered rings, whose ringstructures include at least one heteroatom, preferably one to fourheteroatoms, more preferably one or two heteroatoms. The terms“heterocyclyl” and “heterocyclic” also include polycyclic ring systemshaving two or more cyclic rings in which two or more carbons are commonto two adjoining rings wherein at least one of the rings isheterocyclic, e.g., the other cyclic rings can be cycloalkyls,cycloalkenyls, cycloalkynyls, aryls, heteroaryls, and/or heterocyclyls.Heterocyclyl groups include, for example, piperidine, piperazine,pyrrolidine, morpholine, lactones, lactams, and the like.

The term “heterocyclylalkyl,” as used herein, refers to an alkyl groupsubstituted with a heterocycle group.

The term “hydrocarbyl,” as used herein, refers to a group that is bondedthrough a carbon atom, wherein that carbon atom does not have a ═O or ═Ssubstituent. Hydrocarbyls may optionally include heteroatoms.Hydrocarbyl groups include, but are not limited to, alkyl, alkenyl,alkynyl, alkoxyalkyl, aminoalkyl, aralkyl, aryl, aralkyl, carbocyclyl,cycloalkyl, carbocyclylalkyl, heteroaralkyl, heteroaryl groups bondedthrough a carbon atom, heterocyclyl groups bonded through a carbon atom,heterocyclylakyl, or hydroxyalkyl. Thus, groups like methyl,ethoxyethyl, 2-pyridyl, and trifluoromethyl are hydrocarbyl groups, butsubstituents such as acetyl (which has a ═O substituent on the linkingcarbon) and ethoxy (which is linked through oxygen, not carbon) are not.

The term “hydroxyalkyl,” as used herein, refers to an alkyl groupsubstituted with a hydroxy group.

The term “lower” when used in conjunction with a chemical moiety, suchas, acyl, acyloxy, alkyl, alkenyl, alkynyl, or alkoxy is meant toinclude groups where there are six or fewer non-hydrogen atoms in thesubstituent. A “lower alkyl,” for example, refers to an alkyl group thatcontains six or fewer carbon atoms. In some embodiments, the alkyl grouphas from 1 to 6 carbon atoms, from 1 to 4 carbon atoms, or from 1 to 3carbon atoms. In certain embodiments, acyl, acyloxy, alkyl, alkenyl,alkynyl, or alkoxy substituents defined herein are respectively loweracyl, lower acyloxy, lower alkyl, lower alkenyl, lower alkynyl, or loweralkoxy, whether they appear alone or in combination with othersubstituents, such as in the recitations hydroxyalkyl and aralkyl (inwhich case, for example, the atoms within the aryl group are not countedwhen counting the carbon atoms in the alkyl substituent).

The terms “polycyclyl,” “polycycle”, and “polycyclic” refer to two ormore rings (e.g., cycloalkyls, cycloalkenyls, cycloalkynyls, aryls,heteroaryls, and/or heterocyclyls) in which two or more atoms are commonto two adjoining rings, e.g., the rings are “fused rings”. Each of therings of the polycycle can be substituted or unsubstituted. In certainembodiments, each ring of the polycycle contains from 3 to 10 atoms inthe ring, preferably from 5 to 7.

In the phrase “poly(meta-phenylene oxides),” the term “phenylene” refersinclusively to 6-membered aryl or 6-membered heteroaryl moieties.Exemplary poly(meta-phenylene oxides) are described in the first throughtwentieth aspects of the present disclosure.

The term “silyl” refers to a silicon moiety with three hydrocarbylmoieties attached thereto.

The term “substituted” refers to moieties having substituents replacinga hydrogen on one or more carbons of the backbone. It will be understoodthat “substitution” or “substituted with” includes the implicit provisothat such substitution is in accordance with permitted valence of thesubstituted atom and the substituent, and that the substitution resultsin a stable compound, e.g., which does not spontaneously undergotransformation such as by rearrangement, cyclization, elimination, etc.Moieties that may be substituted can include any appropriatesubstituents described herein, for example, acyl, acylamino, acyloxy,alkoxy, alkoxyalkyl, alkenyl, alkyl, alkylamino, alkylthio, arylthio,alkynyl, amide, amino, aminoalkyl, aralkyl, carbamate, carbocyclyl,cycloalkyl, carbocyclylalkyl, carbonate, ester, ether, heteroaralkyl,heterocyclyl, heterocyclylalkyl, hydrocarbyl, silyl, sulfone, orthioether. As used herein, the term “substituted” is contemplated toinclude all permissible substituents of organic compounds. In a broadaspect, the permissible substituents include acyclic and cyclic,branched and unbranched, carbocyclic and heterocyclic, aromatic andnon-aromatic substituents of organic compounds. The permissiblesubstituents can be one or more and the same or different forappropriate organic compounds. For purposes of this invention, theheteroatoms such as nitrogen may have hydrogen substituents and/or anypermissible substituents of organic compounds described herein whichsatisfy the valences of the heteroatoms. Substituents can include anysubstituents described herein, for example, a halogen, a hydroxyl, acarbonyl (such as a carboxyl, an alkoxycarbonyl, a formyl, or an acyl),a thiocarbonyl (such as a thioester, a thioacetate, or a thioformate),an alkoxy, a phosphoryl, a phosphate, a phosphonate, a phosphinate, anamino, an amido, an amidine, an imine, a cyano, a nitro, an azido, asulfhydryl, an alkylthio, a sulfate, a sulfonate, a sulfamoyl, asulfonamide, a sulfonyl, a heterocyclyl, an aralkyl, or an aromatic orheteroaromatic moiety. In preferred embodiments, the substituents onsubstituted alkyls are selected from C₁₋₆ alkyl, C₃₋₆ cycloalkyl,halogen, carbonyl, cyano, or hydroxyl. In more preferred embodiments,the substituents on substituted alkyls are selected from fluoro,carbonyl, cyano, or hydroxyl. It will be understood by those skilled inthe art that substituents can themselves be substituted, if appropriate.Unless specifically stated as “unsubstituted,” references to chemicalmoieties herein are understood to include substituted variants. Forexample, reference to an “aryl” group or moiety implicitly includes bothsubstituted and unsubstituted variants.

The term “sulfonate” is art-recognized and refers to the group SO₃H, ora pharmaceutically acceptable salt thereof.

The term “sulfone” is art-recognized and refers to the group—S(O)₂—R^(A), wherein R^(A) represents a hydrocarbyl.

The term “thioether,” as used herein, is equivalent to an ether, whereinthe oxygen is replaced with a sulfur.

The term “symmetrical molecule,” as used herein, refers to moleculesthat are group symmetric or synthetic symmetric. The term “groupsymmetric” as used herein, refers to molecules that have symmetryaccording to the group theory of molecular symmetry. The term “syntheticsymmetric,” as used herein, refers to molecules that are selected suchthat no regioselective synthetic strategy is required.

The term “donor,” as used herein, refers to a molecular fragment thatcan be used in organic light emitting diodes and is likely to donateelectrons from its highest occupied molecular orbital to an acceptorupon excitation. In preferred embodiments, donor contain substitutedamino group. In an example embodiment, donors have an ionizationpotential greater than or equal to −6.5 eV.

The term “acceptor,” as used herein, refers to a molecular fragment thatcan be used in organic light emitting diodes and is likely to acceptelectrons into its lowest unoccupied molecular orbital from a donor thathas been subject to excitation. In an example embodiment, acceptors havean electron affinity less than or equal to −0.5 eV.

The term “bridge,” as used herein, refers to a molecular fragment thatcan be included in a molecule which is covalently linked betweenacceptor and donor moieties. The bridge can, for example, be furtherconjugated to the acceptor moiety, the donor moiety, or both. Withoutbeing bound to any particular theory, it is believed that the bridgemoeity can sterically restrict the acceptor and donor moieties into aspecific configuration, thereby preventing the overlap between theconjugated π system of donor and acceptor moieties. Examples of suitablebridge moieties include phenyl, ethenyl, and ethynyl.

The term “multivalent,” as used herein, refers to a molecular fragmentthat is connected to at least two other molecular fragments. Forexample, a bridge moiety, is multivalent.

“

” or “*” as used herein, refers to a point of attachment between twoatoms.

“Hole transport layer (HTL)” and like terms mean a layer made from amaterial which transports holes. High hole mobility is recommended. TheHTL is used to help block passage of electrons transported by theemitting layer. Low electron affinity is typically required to blockelectrons. The HTL should desirably have larger triplets to blockexciton migrations from an adjacent emissive layer (EML). Examples ofHTL compounds include, but are not limited to,di(p-tolyl)aminophenyl]cyclohexane (TAPC), N,N-diphenyl-N,N-bis(3-methylphenyl)-1,1-biphenyl-4,4-diamine (TPD), andN,N′-diphenyl-N,N′-bis(1-naphthyl)- (1,1′-biphenyl)-4,4′-diamine (NPB,α-NPD).

“Emitting layer” and like terms mean a layer which emits light. In someembodiments, the emitting layer comprises a host material and guestmaterial. The guest material can also be referred to as a dopantmaterial, but the disclosure is not limited thereto. The host materialcould be bipolar or unipolar and may be used alone or by combination oftwo or more host materials. The opto-electrical properties of the hostmaterial may differ to which type of guest material (TADF,Phosphorescent or Fluorescent) is used. For Fluorescent guest materials,the host materials should have good spectral overlap between absorptionof the guest material and emission of the host material to induce goodForster transfer to guest materials. For Phosphorescent guest materials,the host materials should have high triplet energy to confine tripletsof the guest material. For TADF guest materials, the host materialsshould have both spectral overlap and higher triplet energy.

“Dopant” and like terms, refer to additive materials for carriertransporting layers, emitting layers or other layers. In carriertransporting layers, dopant and like terms perform as an electronacceptor or a donator that increases the conductivity of an organiclayer of an organic electronic device, when added to the organic layeras an additive. Organic semiconductors may likewise be influenced, withregard to their electrical conductivity, by doping. Such organicsemiconducting matrix materials may be made up either of compounds withelectron-donor properties or of compounds with electron-acceptorproperties. In emitting layers, dopant and like terms also mean thelight emitting material which is dispersed in a matrix, for example, ahost. When a triplet harvesting material is doped into an emitting layeror contained in an adjacent layer so as to improve exciton generationefficiency, it is named as assistant dopant. An assistant dopant maypreferably shorten a lifetime of the exciton. The content of theassistant dopant in the light emitting layer or the adjacent layer isnot particularly limited so long as the triplet harvesting materialimproves the exciton generation efficiency. The content of the assistantdopant in the light emitting layer is preferably higher than, morepreferably at least twice than the light emitting material. In the lightemitting layer, the content of the host material is preferably 50% byweight or more, the content of the assistant dopant is preferably from5% by weight to less than 50% by weight, and the content of the lightemitting material is preferably more than 0% by weight to less titan 30%by weight, more preferably from 0% by weight to less than 10% by weight.The content of the assistant dopant in the adjacent layer may be morethan 50% by weight and may be 100% by weight. In the case where a devicecomprising a triplet harvesting material in a light emitting layer or anadjacent layer has a higher light emission efficiency than a devicewithout the triplet harvesting material, such triplet harvestingmaterial functions as an assistant dopant. A light emitting layercomprising a host material, an assistant dopant and a light emittingmaterial satisfies the following (A) and preferably satisfies thefollowing (B):

ES1(A)>ES1(B)>ES1(C)   (A)

ET1(A)>ET1(B)   (B)

wherein ES1 (A) represents a lowest excited singlet energy level of thehost material; ES1(B) represents a lowest excited singlet energy levelof the assistant dopant; ES1(C) represents a lowest excited singletenergy level of the light emitting material; ET1(A) represents a lowestexcited triplet energy level at 77 K of the host material; and ET1(B)represents a lowest excited triplet energy level at 77 K of theassistant dopant. The assistant dopant has an energy difference ΔE_(ST)between a lowest singlet excited state and a lowest triplet excitedstate at 77 K of preferably 0.3 eV or less, more preferably 0.2 eV orless, still more preferably 0.1 eV or less.

In the compounds of this invention any atom not specifically designatedas a particular isotope is meant to represent any stable isotope of thatatom. Unless otherwise stated, when a position is designatedspecifically as “H” or “hydrogen”, the position is understood to havehydrogen at its natural abundance isotopic composition. Also, unlessotherwise stated, when a position is designated specifically as “d” or“deuterium”, the position is understood to have deuterium at anabundance that is at least 3340 times greater than the natural abundanceof deuterium, which is 0.015% (i.e., at least 50.1% incorporation ofdeuterium).

The term “isotopic enrichment factor” as used herein means the ratiobetween the isotopic abundance and the natural abundance of a specifiedisotope.

In various embodiments, compounds of this invention have an isotopicenrichment factor for each designated deuterium atom of at least 3500(52.5% deuterium incorporation at each designated deuterium atom), atleast 4000 (60% deuterium incorporation), at least 4500 (67.5% deuteriumincorporation), at least 5000 (75% deuterium), at least 5500 (82.5%deuterium incorporation), at least 6000 (90% deuterium incorporation),at least 6333.3 (95% deuterium incorporation), at least 6466.7 (97%deuterium incorporation), at least 6600 (99% deuterium incorporation),or at least 6633.3 (99.5% deuterium incorporation).

The term “isotopologue” refers to a species that differs from a specificcompound of this invention only in the isotopic composition thereof.

The term “compound,” when referring to a compound of this invention,refers to a collection of molecules having an identical chemicalstructure, except that there may be isotopic variation among theconstituent atoms of the molecules. Thus, it will be clear to those ofskill in the art that a compound represented by a particular chemicalstructure containing indicated deuterium atoms, will also contain lesseramounts of isotopologues having hydrogen atoms at one or more of thedesignated deuterium positions in that structure. The relative amount ofsuch isotopologues in a compound of this invention will depend upon anumber of factors including the isotopic purity of deuterated reagentsused to make the compound and the efficiency of incorporation ofdeuterium in the various synthesis steps used to prepare the compound.However, as set forth above the relative amount of such isotopologues intoto will be less than 49.9% of the compound. In other embodiments, therelative amount of such isotopologues in toto will be less than 47.5%.less than 40%, less than 32.5%, less than 25%, less than 17.5%, lessthan 10%, less than 5%, less than 3%, less than 1%, or less than 0.5% ofthe compound.

“Substituted with deuterium” refers to the replacement of one or morehydrogen atoms with a corresponding number of deuterium atoms. “D” and“d” both refer to deuterium.

Principles of OLED

OLEDs are typically composed of a layer of organic materials orcompounds between two electrodes, an anode and a cathode. The organicmolecules are electrically conductive as a result of delocalization of πelectronics caused by conjugation over part or all of the molecule. Whenvoltage is applied, electrons from the highest occupied molecularorbital (HOMO) present at the anode flow into the lowest unoccupiedmolecular orbital (LUMO) of the organic molecules present at thecathode. Removal of electrons from the HOMO is also referred to asinserting electron holes into the HOMO. Electrostatic forces bring theelectrons and the holes towards each other until they recombine and forman exciton (which is the bound state of the electron and the hole). Asthe excited state decays and the energy levels of the electrons relax,radiation having a frequency in the visible spectrum is emitted. Thefrequency of this radiation depends on the band gap of the material,which is the difference in energy between the HOMO and the LUMO.

As electrons and holes are fermions with half integer spin, an excitonmay either be in a singlet state or a triplet state depending on how thespins of the electron and hole have been combined. Statistically, threetriplet excitons will be formed for each singlet exciton. Decay fromtriplet states is spin forbidden, which results in increases in thetimescale of the transition and limits the internal efficiency offluorescent devices. Phosphorescent organic light-emitting diodes makeuse of spin-orbit interactions to facilitate intersystem crossingbetween singlet and triplet states, thus obtaining emission from bothsinglet and triplet states and improving the internal efficiency.

One prototypical phosphorescent material is iridiumtris(2-phenylpyridine) (Ir(ppy)₃) in which the excited state is a chargetransfer from the Ir atom to the organic ligand. Such approaches havereduced the triplet lifetime to about several μs, several orders ofmagnitude slower than the radiative lifetimes of fully-allowedtransitions such as fluorescence. Ir-based phosphors have proven to beacceptable for many display applications, but losses due to largetriplet densities still prevent the application of OLEDs to solid-statelighting at higher brightness.

Thermally activated delayed fluorescence (TADF) seeks to minimizeenergetic splitting between singlet and triplet states (Δ, ΔE_(ST)). Thereduction in exchange splitting from typical values of 0.4-0.7 eV to agap of the order of the thermal energy (proportional to kBT, where kBrepresents the Boltzmann constant, and T represents temperature) meansthat thermal agitation can transfer population between singlet levelsand triplet levels in a relevant timescale even if the coupling betweenstates is small.

TADF molecules consist of donor and acceptor moieties connected directlyby a covalent bond or via a conjugated linker (or “bridge”). A “donor”moiety is likely to transfer electrons from its HOMO upon excitation tothe “acceptor” moiety. An “acceptor” moiety is likely to accept theelectrons from the “donor” moiety into its LUMO. The donor-acceptornature of TADF molecules results in low-lying excited states withcharge-transfer character that exhibit very low ΔE_(ST). Since thermalmolecular motions can randomly vary the optical properties ofdonor-acceptor systems, a rigid three-dimensional arrangement of donorand acceptor moieties can be used to limit the non-radiative decay ofthe charge-transfer state by internal conversion during the lifetime ofthe excitation.

It is beneficial, therefore, to decrease ΔE_(ST), and to create a systemwith increased reversed intersystem crossing (RISC) capable ofexploiting triplet excitons. Such a system, it is believed, will resultin increased quantum efficiency and decreased emission lifetimes.Systems with these features will be capable of emitting light withoutbeing subject to the rapid degradation prevalent in OLEDs known today.

Compounds of the Disclosure

In some embodiments, the compounds have a structure of Formula (I).

wherein

two of Z¹, Z², Z³, Z⁴ and Z⁵ are independently A,

the other remaining three of Z¹, Z², Z³, Z⁴ and Z⁵ are independentlyselected from H, deuterium, substituted or unsubstituted alkyl, and A,

A is selected from CN, substituted or unsubstituted aryl having at leastone cyano, and substituted or unsubstituted heteroaryl having at leastone nitrogen atom as a ring-constituting atom,

two of R¹, R², R³ and R⁴ are independently D,

the other remaining two of R¹, R², R³ and R⁴ are selected from H,deuterium, substituted or unsubstituted alkyl, substituted orunsubstituted aryl, substituted or unsubstituted heteroaryl, and D,

D is group of Formula (IIa), (IIb), (IIc) or (IId):

R^(D) is independently selected from hydrogen, deuterium, substituted orunsubstituted alkyl, substituted or unsubstituted alkoxy, substituted orunsubstituted amino, substituted or unsubstituted aryl, substituted orunsubstituted aryloxy, substituted or unsubstituted heteroaryl,substituted or unsubstituted heteroaryloxy, and silyl; two or moreinstances of R^(D) taken together can form a ring system;

R^(D′) is independently selected from hydrogen, deuterium, substitutedor unsubstituted alkyl, substituted or unsubstituted amino, substitutedor unsubstituted aryl, and substituted or unsubstituted heteroaryl; twoor more instances of R^(D′) and R_(D) taken together can form a ringsystem;

L^(D) is independently selected from single bond, substituted orunsubstituted arylene, and substituted or unsubstituted heteroarylene;wherein each instance of arylene and heteroarylene can be substitutedwith one or more substituents independently selected from deuterium,substituted or unsubstituted alkyl, substituted or unsubstituted aryl,and substituted or unsubstituted heteroaryl; two or more of thesesubstituents taken together can form a ring system;

C—R^(D) of the benzene rings in Formulae (IIa), (IIb), (IIc) and (IId)may be substituted with N; and

each “*” represents a point of attachment to Formula (I).

In some embodiments, alkyl is C1-C20-alkyl. In some embodiments, alkylis C1-C12 alkyl. In some embodiments, alkyl is C1-C6 alkyl. In someembodiments, alkyl is C1-C3 alkyl. In some embodiments, aryl is C6-C40aryl. In some embodiments, aryl is C6-C25 aryl. In some embodiments,aryl is C6-C14 aryl. In some embodiments, aryl is C6-C10 aryl. In someembodiments, heteroaryl is C2-C40 heteroaryl. In some embodiments,heteroaryl has 5-40 ring-constituting atoms. In some embodiments,heteroaryl has 5-25 ring-constituting atoms. In some embodiments,heteroaryl has 5-10 ring-constituting atoms. In some embodiments, alkoxyis C1-C20 alkoxy. In some embodiments, alkoxy is C1-C12 alkoxy. In someembodiments, alkoxy is C1-C6 alkoxy. In some embodiments, alkoxy isC1-C3 alkoxy. In some embodiments, aryloxy is C6-C40 aryloxy. In someembodiments, aryloxy is C6-C25 aryloxy. In some embodiments, aryloxy isC6-C14 aryloxy. In some embodiments, aryloxy is C6-C10 aryloxy. In someembodiments, heteroaryloxy is C3-C40 heteroaryloxy. In some embodiments,heteroaryloxy has 5-40 ring-constituting atoms. In some embodiments,heteroaryloxy has 5-25 ring-constituting atoms. In some embodiments,heteroaryloxy has 5-10 ring-constituting atoms. In some embodiments,arylene is C6-C40 arylene. In some embodiments, arylene is C6-C25arylene. In some embodiments, arylene is C6-C14 arylene. In someembodiments, arylene is C6-C10 arylene. In some embodiments,heteroarylene is C2-C40 heteroarylene. In some embodiments,heteroarylene has 5-40 ring-constituting atoms. In some embodiments,heteroarylene has 5-25 ring-constituting atoms. In some embodiments,heteroarylene has 5-10 ring-constituting atoms.

In Formula (I), at least two of Z¹, Z², Z³, Z⁴ and Z⁵ are independentlyA. In some embodiments, Z¹ and Z² are independently A, and the othersare not A. In some embodiments, Z² and Z³ are independently A, and theothers are not A. In some embodiments, Z¹ and Z³ are independently A,and the others are not A. In some embodiments, Z¹ and Z⁴ areindependently A, and the others are not A. In some embodiments, Z¹ andZ⁵ are independently A, and the others are not A. In some embodiments,Z² and Z⁴ are independently A, and the others are not A. In someembodiments, Z¹, Z² and Z³ are independently A, and the others are notA. In some embodiments, Z¹, Z² and Z⁴ are independently A, and theothers are not A. In some embodiments, Z¹, Z² and Z⁵ are independentlyA, and the others are not A. In some embodiments, Z¹, Z³ and Z⁴ areindependently A, and the others are not A. In some embodiments, Z¹, Z³and Z⁵ are independently A, and the others are not A. In someembodiments, Z², Z³ and Z⁴ are independently A, and the others are notA. In some embodiments, Z¹, Z², Z³ and Z⁴ are independently A, and Z⁵ isnot A. In some embodiments, Z¹, Z², Z³ and Z⁵ are independently A, andZ⁴ is not A. In some embodiments, Z¹, Z², Z⁴ and Z⁵ are independently A,and Z³ is not A. In some embodiments, Z¹, Z², Z³, Z⁴ and Z⁵ areindependently A.

In some embodiments, all A's existing as Z¹, Z², Z³, Z⁴ and/or Z⁵ arethe same. In some embodiments, all A's existing as Z¹, Z², Z³, Z⁴ and/orZ⁵ are not the same. In some embodiments, all A's existing as Z¹, Z²,Z³, Z⁴ and/or Z⁵ differ from each other. In some embodiments, all A'sexisting as Z¹, Z², Z³, Z⁴ and/or Z⁵ are CN. In some embodiments, allA's existing as Z¹, Z², Z³, Z⁴ and/or Z⁵ are independently substitutedor unsubstituted aryl having at least one cyano. In some embodiments,all A's existing as Z¹, Z², Z³, Z⁴ and/or Z⁵ are independently CN orsubstituted or unsubstituted aryl having at least one cyano. In someembodiments, all A's existing as Z¹, Z², Z³, Z⁴ and/or Z⁵ areindependently substituted or unsubstituted heteraryl having at least onenitrogen atom as a ring-constituting atom.

In some embodiments, two of Z¹, Z², Z³, Z⁴ and/or Z⁵ are independentlyA, and the other remaining three are H. In some embodiments, two of Z¹,Z², Z³, Z⁴ and/or Z⁵ are independently A, and the other remaining threeare deuterium. In some embodiments, two of Z¹, Z², Z³, Z⁴ and/or Z⁵ areindependently A, and the other remaining three are independentlysubstituted or unsubstituted aryl. In some embodiments, two of Z¹, Z²,Z³, Z⁴ and/or Z⁵ are independently A, and the other remaining three areindependently H or substituted or unsubstituted aryl. In someembodiments, three of Z¹, Z², Z³, Z⁴ and/or Z⁵ are independently A, andthe other remaining two are H. In some embodiments, three of Z¹, Z², Z³,Z⁴ and/or Z⁵ are independently A, and the other remaining two aredeuterium. In some embodiments, three of Z¹, Z², Z³, Z⁴ and/or Z⁵ areindependently A, and the other remaining two are independentlysubstituted or unsubstituted aryl. In some embodiments, three of Z¹, Z²,Z³, Z⁴ and/or Z⁵ are independently A, other one is H, and the otherremaining one is substituted or unsubstituted aryl. In some embodiments,four of Z¹, Z², Z³, Z⁴ and/or Z⁵ are independently A, the otherremaining one is H. In some embodiments, four of Z¹, Z², Z³, Z⁴ and/orZ⁵ are independently A, the other remaining one is deuterium. In someembodiments, four of Z¹, Z², Z³, Z⁴ and/or Z⁵ are independently A, theother remaining one is substituted or unsubstituted aryl.

In some embodiments, the substituted or unsubstituted aryl having atleast one cyano is substituted or unsubstituted 4-cyanophenyl,substituted or unsubstituted 3-cyanophenyl, substituted or unsubstituted2-cyanophenyl, or substituted or unsubstituted 3,5-dicyanophenyl. Insome embodiments, the substituted or unsubstituted aryl having at leastone cyano is unsubstituted 4-cyanophenyl, unsubstituted 3-cyanophenyl,unsubstituted 2-cyanophenyl, or unsubstituted 3,5-dicyanophenyl.

In some embodiments, the substituted or unsubstituted heteroaryl havingat least one nitrogen atom as a ring-constituting atom is

In some embodiments, the substituted or unsubstituted heteroaryl havingat least one nitrogen atom as a ring-constituting atom is

In some embodiments, the substituted or unsubstituted heteroaryl havingat least one nitrogen atom as a ring-constituting atom is

In some embodiments, the substituted or unsubstituted heteroaryl havingat least one nitrogen atom as a ring constituting atom is

In some embodiments, the substituted or unsubstituted heteroaryl havingat least one nitrogen atom as a ring-constituting atom is

R¹¹, R¹², R¹³, R¹⁴ and R¹⁵ are independently H or substituent, L11 issingle bond or substituent.

In some embodiments, R¹¹, R¹², R¹³, R¹⁴ and R¹⁵ are independently H, CN,substituted or unsubstituted alkyl, substituted or unsubstituted aryl,or substituted or unsubstituted heteroaryl. Each instance of alkyl canbe substituted with one or more substituents independently selected fromdeuterium, substituted or unsubstituted aryl, and substituted orunsubstituted heteroaryl. Each instance of aryl and heteroaryl can besubstituted with one or more substituents independently selected fromdeuterium, substituted or unsubstituted alkyl, substituted orunsubstituted aryl, and substituted or unsubstituted heteroaryl. Two ormore of these substituents taken together can form a ring system. Insome embodiments, the ring system here is substituted or unsubstitutedaromatic ring, or substituted or unsubstituted aliphatic ring.

In some embodiments, L¹¹ is selected from single bond, substituted orunsubstituted arylene, and substituted or unsubstituted heteroarylene.In some embodiments, each instance of arylene and heteroarylene issubstituted with one or more substituents independently selected fromdeuterium, substituted or unsubstituted alkyl, substituted orunsubstituted aryl, and substituted or unsubstituted heteroaryl; and twoor more of these substituents taken together can form a ring system. Insome embodiments, the ring system here is substituted or unsubstitutedaromatic ring, or substituted or unsubstituted aliphatic ring. In someembodiments, L¹¹ is single bond, unsubstituted phenylene, or phenylenesubstituted with at least one alkyl.

In some embodiments, A is selected from the group consisting of A1 to A9shown below.

In Formula (I), at least two of R¹, R², R³ and R⁴ are independently D.In some embodiments, R¹ and R² are independently D, and R³ and R⁴ arenot D. In some embodiments, R¹ and R³ are independently D, and R² and R⁴are not D. In some embodiments, R¹ and R⁴ are independently D, and R²and R³ are not D. In some embodiments, R² and R³ are independently D,and R¹ and R⁴ are not D. In some embodiments, R¹, R² and R³ areindependently D, and R⁴ is not D. In some embodiments, R¹, R² and R⁴ areindependently D, and R³ is not D. In some embodiments, R¹, R², R³ and R⁴are independently D.

In some embodiments, all D's existing as R¹, R², R³ and/or R⁴ are thesame. In some embodiments, all D's existing as R¹, R², R³ and/or R⁴ arenot the same. In some embodiments, all D's existing as R¹, R², R³ and/orR⁴ differ from each other. In some embodiments, all D's existing as R¹,R², R³ and/or R⁴ are independently group of Formula (IIa). In someembodiments, all D's existing as R¹, R², R³ and/or R⁴ are independentlygroup of Formula (IIb). In some embodiments, all D's existing as R¹, R²,R³ and/or R⁴ are independently group of Formula (IIc). In someembodiments, all D's existing as R¹, R², R³ and/or R⁴ are independentlygroup of Formula (IId).

In some embodiments, two of R¹, R², R³ and R⁴ are independently D, andthe other remaining two are H. In some embodiments, two of R¹, R², R³and R⁴ are independently D, and the other remaining two are deuterium.In some embodiments, two of R¹, R², R³ and R⁴ are independently D, andthe other remaining two are independently substituted or unsubstitutedalkyl. In some embodiments, two of R¹, R², R³ and R⁴ are independentlyD, and the other remaining two are independently substituted orunsubstituted aryl. In some embodiments, two of R¹, R², R³ and R⁴ areindependently D, and the other remaining two are independentlysubstituted or unsubstituted heteroaryl. In some embodiments, two of R¹,R², R³ and R⁴ are independently D, other one is H, and the otherremaining one is substituted or unsubstituted alkyl. In someembodiments, two of R¹, R², R³ and R⁴ are independently D, other one isH, and the other remaining one is substituted or unsubstituted aryl. Insome embodiments, two of R¹, R², R³ and R⁴ are independently D, otherone is H, and the other remaining one is substituted or unsubstitutedheteroaryl. In some embodiments, three of R¹, R², R³ and R⁴ areindependently D, and the other remaining one is H. In some embodiments,three of R¹, R², R³ and R⁴ are independently D, and the other remainingone is deuterium. In some embodiments, three of R¹, R², R³ and R⁴ areindependently D, and the other remaining one is independentlysubstituted or unsubstituted alkyl. In some embodiments, three of R¹,R², R³ and R⁴ are independently D, and the other remaining one isindependently substituted or unsubstituted aryl. In some embodiments,three of R¹, R², R³ and R⁴ are independently D, and the other remainingone is independently substituted or unsubstituted heteroaryl.

In some embodiments, D is group of Formula (IIa). In some embodiments, Dis group of Formula (IIb). In some embodiments, D is group of Formula(IIc). In some embodiments, D is group of Formula (IId).

In some embodiments, R^(D) are hydrogen. In some embodiments, R^(D) aredeuterium. In some embodiments, R^(D) are independently hydrogen orsubstituted or unsubstituted alkyl. In some embodiments, R^(D) areindependently hydrogen or substituted or unsubstituted alkoxy. In someembodiments, R^(D) are independently hydrogen or substituted orunsubstituted amino. In some embodiments, R^(D) are independentlyhydrogen or substituted or unsubstituted aryl. In some embodiments,R^(D) are independently hydrogen or substituted or unsubstitutedaryloxy. In some embodiments, R^(D) are independently hydrogen orsubstituted or unsubstituted heteroaryl. In some embodiments, R^(D) areindependently hydrogen or substituted or unsubstituted heteroaryloxy. Insome embodiments, R^(D) are independently hydrogen or silyl. In someembodiments, two or more instances of R^(D) are taken together to form aring system.

In some embodiments of Formula (IIa), R^(D) at 3-position of thediphenylamino is substituted and the other R^(D) are hydrogen. In someembodiments of Formula (IIa), R^(D) at 3- and 3′-positions of thediphenylamino are substituted and the other R^(D) are hydrogen. In someembodiments of Formula (IIa), R^(D) at 1-position of the diphenylaminoand R^(D) at 2-position of the diphenylamino are taken together to forma ring system. In some embodiments of Formula (IIa), R^(D) at 2-positionof the diphenylamino and R^(D) at 3-position of the diphenylamino aretaken together to form a ring system. In some embodiments of Formula(IIa), R^(D) at 3-position of the diphenylamino and R^(D) at 4-positionof the diphenylamino are taken together to form a ring system.

In some embodiments of Formulae (IIb) and (IIc), R^(D) at 3-position ofthe carbazole ring is substituted and the other R^(D) are hydrogen. Insome embodiments of Formulae (IIb) and (IIc), R^(D) at 3- and6-positions of the carbazole ring are substituted and the other R^(D)are hydrogen. In some embodiments of Formulae (IIb) and (IIc), R^(D) at1-position of the carbazole ring and R^(D) at 2-position of thecarbazole ring are taken together to form a ring system. In someembodiments of Formulae (IIb) and (IIc), R^(D) at 2-position of thecarbazole ring and R^(D) at 3-position of the carbazole ring are takentogether to form a ring system. In some embodiments of Formulae (IIb)and (IIc), R^(D) at 3-position of the carbazole ring and R^(D) at4-position of the carbazole ring are taken together to form a ringsystem.

In some embodiments of Formula (IIc), L^(D) bonds to 5-position of thecarbazole ring. In some embodiments of Formula (IIc), L^(D) bonds to6-position of the carbazole ring. In some embodiments of Formula (IIc),L^(D) bonds to 7-position of the carbazole ring. In some embodiments ofFormula (IIc), L^(D) bonds to 8-position of the carbazole ring.

In some embodiments of Formula (IId), R^(D) at 2-position of the indolering is substituted and the other R^(D) are hydrogen. In someembodiments of Formula (IId), R^(D) at 3-position of the indole ring issubstituted and the other R^(D) are hydrogen. In some embodiments ofFormula (IId), R^(D) at 2- and 3-positions of the indole ring aresubstituted and the other R^(D) are hydrogen. In some embodiments ofFormula (IId), R^(D) at 2-position of the indole ring and R^(D) at3-position of the indole ring are taken together to form a ring system.In some embodiments of Formula (IId), R^(D) at 3-position of the indolering and R^(D) at 4-position of the indole ring are taken together toform a ring system.

In some embodiments, R^(D′)is hydrogen. In some embodiments, R^(D′)isdeuterium. In some embodiments, R^(D′)is substituted or unsubstitutedalkyl. In some embodiments, R^(D′)is substituted or unsubstituted amino.In some embodiments, R^(D′)is substituted or unsubstituted aryl. In someembodiments, R^(D′)is substituted or unsubstituted heteroaryl. In someembodiments, two or more instances of R^(D′)and R^(D) taken together canform a ring system.

In some embodiments, L^(D) is a single bond. In some embodiments, L^(D)is substituted or unsubstituted arylene. In some embodiments, L^(D) issubstituted or unsubstituted heteroarylene.

C—R^(D) of the benzene rings in Formulae (IIa), (IIb), (IIc) and (IId)may be substituted with N. In some embodiments, only one of C—R^(D) ofthe benzene ring is substituted.

Each “*” in Formulae (IIa), (IIb), (IIc) and (IId) represents a point ofattachment to Formula (I).

In some embodiments, D is selected from the group consisting of D1 toD77 shown below wherein Ph is unsubstituted phenyl,

In some embodiments, Z¹ and Z² are independently A, and R¹ and R² areindependently D. In some embodiments, Z¹ and Z² are independently A, andR¹ and R³ are independently D. In some embodiments, Z¹ and Z² areindependently A, and R¹ and R⁴ are independently D. In some embodiments,Z¹ and Z² are independently A, and R² and R³ are independently D. Insome embodiments, Z¹ and Z² are independently A, and R¹ and R² and R³are independently D. In some embodiments, Z¹ and Z² are independently A,and R¹, R² and R⁴ are independently D. In some embodiments, Z¹ and Z²are independently A, and R¹, R² and R³ are independently D. In someembodiments, Z¹ and Z² are independently A, and D¹, D², D³ and D⁴ areindependently D. In some embodiments, Z² and Z³ are independently A, andR¹ and R² are independently D. In some embodiments, Z² and Z³ areindependently A, and R¹ and R³ are independently D. In some embodiments,Z² and Z³ are independently A, and R¹ and R⁴ are independently D. Insome embodiments, Z² and Z³ are independently A, and R² and R³ areindependently D. In some embodiments, Z² and Z³ are independently A, andR¹, R² and R³ are independently D. In some embodiments, Z² and Z³ areindependently A, and R¹, R² and R⁴ are independently D. In someembodiments, Z² and Z³ are independently A, and R¹, R² and R³ areindependently D. In some embodiments, Z² and Z³ are independently A, andD¹, D², D³ and D⁴ are independently D.

In some embodiments, the compound of Formula (I) is selected fromCompounds 1 to 506 shown in the following tables:

Z¹ Z² Z³ Z⁴ Z⁵ R¹ R² R³ R⁴  1 A1 A1 H H H D1 D1 D1 D1  2 A1 A1 H H H D2D2 D2 D2  3 A1 A1 H H H D3 D3 D3 D3  4 A1 A1 H H H D4 D4 D4 D4  5 A1 A1H H H D5 D5 D5 D5  6 A1 A1 H H H D6 D6 D6 D6  7 A1 A1 H H H D7 D7 D7 D7 8 A1 A1 H H H D8 D8 D8 D8  9 A1 A1 H H H D9 D9 D9 D9  10 A1 A1 H H HD10 D10 D10 D10  11 A1 A1 H H H D11 D11 D11 D11  12 A1 A1 H H H D1 D1 PhD1  13 A1 A1 H H H D2 D2 Ph D2  14 A1 A1 H H H D3 D3 Ph D3  15 A1 A1 H HH D4 D4 Ph D4  16 A1 A1 H H H D1 D11 Ph D1  17 A1 A1 H H H D1 D5 Ph D1 18 A1 A1 H H H D11 D1 Ph D11  19 A1 A1 H H H D11 D11 Ph D11  20 A1 A1 HH H D5 D5 Ph D5  21 A1 A1 H H H H D5 Ph D5  22 A1 A1 H H H H D1 D1 D11 23 A1 A1 H H H H D1 D1 D1  24 A1 A1 H H H H D1 D1 D4  25 A1 A1 H H H HD1 D1 D5  26 A1 A1 H H H H D1 D1 H  27 A1 A1 H H H H D11 D11 H  28 A1 A1H H H H D11 Ph D11  29 A1 A1 H H H H D1 Ph D1  30 A1 A1 H H H H D11 D11D1  31 A1 A1 H H H H D11 D11 D11  32 A1 A1 H H H H D3 D3 H  33 A1 A1 H HH H D4 D4 H  34 A1 A1 H H H H D5 D5 H  35 A1 A1 H H H H D4 D4 D1  36 A1A1 H H H H D5 D5 D1  37 A1 A1 H H H H D5 D5 D5  38 A1 A1 H H H D4 Ph D1D4  39 A1 A1 H H H D1 Ph D4 D1  40 A1 A1 H H H D3 Ph Ph D3  41 A1 A1 H HH D4 Ph D1 D4  42 A1 A1 H H H D5 D1 Ph D5  43 A1 A1 H H H H D11 D11 D11 44 A1 A1 H H H H D3 D3 D3  45 A1 A1 H H H H D6 D6 H  46 A1 A1 H H H HD22 D22 H  47 A1 A1 H H H H D52 D62 H  48 A1 A1 H H H H D60 D60 H  49 A1A1 H H H H D70 D70 H  50 A1 A1 H H H Ph D1 D1 Ph  51 A1 A1 H H H Ph D5D5 Ph  52 H A1 A1 H H D5 D11 Ph D5  53 H A1 A1 H H D1 D1 D1 D1  54 H A1A1 H H D2 D2 D2 D2  55 H A1 A1 H H D3 D3 D3 D3  56 H A1 A1 H H D4 D4 D4D4  57 H A1 A1 H H D5 D5 D5 D5  58 H A1 A1 H H D6 D6 D6 D6  59 H A1 A1 HH D7 D7 D7 D7  60 H A1 A1 H H D8 D8 D8 D8  61 H A1 A1 H H D9 D9 D9 D9 62 H A1 A1 H H D10 D10 D10 D10  63 H A1 A1 H H D11 D11 D11 D11  64 H A1A1 H H D5 D1 Ph D5  65 H A1 A1 H H D11 D1 Ph D11  66 H A1 A1 H H D3 D1Ph D3  67 H A1 A1 H H D4 D1 Ph D4  68 H A1 A1 H H H D1 D1 D11  69 H A1A1 H H H D1 D1 D1  70 H A1 A1 H H H D1 D1 D4  71 H A1 A1 H H H D1 D1 D5 72 H A1 A1 H H H D1 D1 H  73 H A1 A1 H H H D11 D11 H  74 H A1 A1 H H HD11 Ph D11  75 H A1 A1 H H H D1 Ph D1  76 H A1 A1 H H H D5 Ph D5  77 HA1 A1 H H H D11 D11 D1  78 H A1 A1 H H H D11 D11 D11  79 H A1 A1 H H HD3 D3 H  80 H A1 A1 H H H D4 D4 H  81 H A1 A1 H H H D5 D5 H  82 H A1 A1H H H D4 D4 D1  83 H A1 A1 H H H D5 D5 D1  84 H A1 A1 H H H D5 D5 D5  85H A1 A1 H H D1 Ph D1 D1  86 H A1 A1 H H D1 Ph D11 D1  87 H A1 A1 H H D1Ph D4 D1  88 H A1 A1 H H D1 Ph D5 D1  89 H A1 A1 H H D11 Ph D11 D11  90H A1 A1 H H H D3 D3 D3  91 A1 H H A1 H D1 D1 D1 D1  92 A1 H H A1 H D4 D4D4 D4  93 A1 H H A1 H D5 D5 D5 D5  94 A1 H H A1 H D11 D11 D11 D11  95 A1H H A1 H H D1 D1 D11  96 A1 H H A1 H H D1 D1 D1  97 A1 H H A1 H H D1 D1D4  98 A1 H H A1 H H D1 D1 D5  99 A1 H H A1 H H D1 D1 H 100 A1 H H A1 HH D11 D11 H 101 A1 H H A1 H H D11 Ph D11 102 A1 H H A1 H H D1 Ph D1 103A1 H H A1 H H D5 Ph D5 104 A1 H H A1 H H D11 D11 D1 105 A1 H H A1 H HD11 D11 D11 106 A1 H H A1 H H D3 D3 H 107 A1 H H A1 H H D4 D4 H 108 A1 HH A1 H H D5 D5 H 109 A1 H H A1 H H D4 D4 D1 110 A1 H H A1 H H D5 D5 D1111 A1 H H A1 H H D5 D5 D5 112 A1 H H A1 H D4 Ph D1 D4 113 A1 H H A1 HD1 Ph D1 D1 114 A1 H H A1 H D1 Ph D11 D1 115 A1 H H A1 H D1 Ph D4 D1 116A1 H H A1 H D1 Ph D5 D1 117 A1 H H A1 H D11 Ph D1 D11 118 A1 H H A1 HD11 Ph D11 D11 119 A1 H H A1 H H D11 D11 H 120 A1 H H A1 H H D3 D3 D3121 A1 H H A1 H H D5 Ph D5 122 A1 H A1 H H D1 D1 D1 D1 123 A1 H A1 H HD4 D4 D4 D4 124 A1 H A1 H H D5 D5 D5 D5 125 A1 H A1 H H D11 D11 D11 D11126 A1 H A1 H H H D11 D11 H 127 A1 H A1 H H H D11 Ph D11 128 A1 H A1 H HH D1 Ph D1 129 A1 H A1 H H H D5 Ph D5 130 A1 H A1 H H H D11 D11 D1 131A1 H A1 H H H D11 D11 D11 132 A1 H A1 H H H D3 D3 H 133 A1 H A1 H H H D4D4 H 134 A1 H A1 H H H D5 D5 H 135 A1 H A1 H H H D4 D4 D1 136 A1 H A1 HH H D5 D5 D1 137 A1 H A1 H H H D5 D5 D5 138 A1 H A1 H H D4 Ph D1 D4 139A1 H A1 H H D1 Ph D1 D1 140 A1 H A1 H H D1 Ph D11 D1 141 A1 H A1 H H D1Ph D4 D1 142 A1 H A1 H H D1 Ph D5 D1 143 A1 H A1 H H D11 Ph D1 D11 144A1 H A1 H H D11 Ph D11 D11 145 A1 H A1 H H D3 D3 Ph D3 146 A1 H A1 H HD5 D1 Ph D5 147 A1 H A1 H H H D1 D1 D1 148 A1 H A1 H H H D1 D1 D11 149A1 H A1 H H H D1 D1 D4 150 A1 H A1 H H H D1 D1 D5 151 A1 H A1 H H H D1D1 H 152 A1 H A1 H H H D3 D3 D3 153 A1 H H H A1 D1 D1 D1 D1 154 A1 H H HA1 D4 D4 D4 D4 155 A1 H H H A1 D5 D5 D5 D5 156 A1 H H H A1 D11 D11 D11D11 157 A1 H H H A1 H D11 D11 H 158 A1 H H H A1 H D11 Ph D11 159 A1 H HH A1 H D1 Ph D1 160 A1 H H H A1 H D5 Ph D5 161 A1 H H H A1 H D11 D11 D1162 A1 H H H A1 H D11 D11 D11 163 A1 H H H A1 H D3 D3 H 164 A1 H H H A1H D4 D4 H 165 A1 H H H A1 H D5 D5 H 166 A1 H H H A1 H D4 D4 D1 167 A1 HH H A1 H D5 D5 D1 168 A1 H H H A1 H D5 D5 D5 169 A1 H H H A1 D4 Ph D1 D4170 A1 H H H A1 D1 Ph D1 D1 171 A1 H H H A1 D1 Ph D11 D1 172 A1 H H H A1D1 Ph D4 D1 173 A1 H H H A1 D1 Ph D5 D1 174 A1 H H H A1 D11 Ph D1 D11175 A1 H H H A1 D11 Ph D11 D11 176 A1 H H H A1 D3 D3 Ph D3 177 A1 H H HA1 D5 D1 Ph D5 178 A1 H H H A1 H D1 D1 D1 179 A1 H H H A1 H D1 D1 D11180 A1 H H H A1 H D1 D1 D4 181 A1 H H H A1 H D1 D1 D5 182 A1 H H H A1 HD1 D1 H 183 A1 H H H A1 H D3 D3 D3 184 A1 H A2 H H D1 D1 D1 D1 185 A1 HA4 H H D1 D1 D1 D1 186 A1 H A6 H H D1 D1 D1 D1 187 A1 H A9 H H D1 D1 D1D1 188 A1 A2 H H H D1 D1 D1 D1 189 A1 A4 H H H D1 D1 D1 D1 190 A1 A6 H HH D1 D1 D1 D1 191 A1 A9 H H H D1 D1 D1 D1 192 A1 H H A2 H D1 D1 D1 D1193 A1 H H A4 H D1 D1 D1 D1 194 A1 H H A6 H D1 D1 D1 D1 195 A1 H H A9 HD1 D1 D1 D1 196 A1 H H H A2 D1 D1 D1 D1 197 A1 H H H A4 D1 D1 D1 D1 198A1 H H H A6 D1 D1 D1 D1 199 A1 H H H A9 D1 D1 D1 D1 200 A1 H A2 H H D1Ph D1 D1 201 A1 H A4 H H D1 Ph D1 D1 202 A1 H A6 H H D1 Ph D1 D1 203 A1H A9 H H D1 Ph D1 D1 204 A1 A2 H H H D1 Ph D1 D1 205 A1 A4 H H H D1 PhD1 D1 206 A1 A6 H H H D1 Ph D1 D1 207 A1 A9 H H H D1 Ph D1 D1 208 A1 H HA2 H D1 Ph D1 D1 209 A1 H H A4 H D1 Ph D1 D1 210 A1 H H A6 H D1 Ph D1 D1211 A1 H H A9 H D1 Ph D1 D1 212 A1 H H H A2 D1 Ph D1 D1 213 A1 H H H A4D1 Ph D1 D1 214 A1 H H H A6 D1 Ph D1 D1 215 A1 H H H A9 D1 Ph D1 D1 216H A1 A2 H H D1 D1 Ph D1 217 H A1 A4 H H D1 D1 Ph D1 218 H A1 A6 H H D1D1 Ph D1 219 H A1 A9 H H D1 D1 Ph D1 220 A1 H A2 H H H D1 Ph D1 221 A1 HA4 H H H D1 Ph D1 222 A1 H A6 H H H D1 Ph D1 223 A1 H A9 H H H D1 Ph D1224 A1 A2 H H H H D1 Ph D1 225 A1 A4 H H H H D1 Ph D1 226 A1 A6 H H H HD1 Ph D1 227 A1 A9 H H H H D1 Ph D1 228 A1 H H A2 H H D1 Ph D1 229 A1 HH A4 H H D1 Ph D1 230 A1 H H A6 H H D1 Ph D1 231 A1 H H A9 H H D1 Ph D1232 A1 H H H A2 H D1 Ph D1 233 A1 H H H A4 H D1 Ph D1 234 A1 H H H A6 HD1 Ph D1 235 A1 H H H A9 H D1 Ph D1 236 A1 H A2 H H H D1 D1 H 237 A1 HA4 H H H D1 D1 H 238 A1 H A6 H H H D1 D1 H 239 A1 H A9 H H H D1 D1 H 240A1 A2 H H H H D1 D1 H 241 A1 A4 H H H H D1 D1 H 242 A1 A6 H H H H D1 D1H 243 A1 A9 H H H H D1 D1 H 244 A1 H H A2 H H D1 D1 H 245 A1 H H A4 H HD1 D1 H 246 A1 H H A6 H H D1 D1 H 247 A1 H H A9 H H D1 D1 H 248 A1 H H HA2 H D1 D1 H 249 A1 H H H A4 H D1 D1 H 250 A1 H H H A6 H D1 D1 H 251 A1H H H A9 H D1 D1 H 252 A1 A2 H H H H Ph D1 D1 253 A1 A4 H H H H Ph D1 D1254 A1 A6 H H H H Ph D1 D1 255 A1 A9 H H H H Ph D1 D1 256 A1 H H A2 H HPh D1 D1 257 A1 H H A4 H H Ph D1 D1 258 A1 H H A6 H H Ph D1 D1 259 A1 HH A9 H H Ph D1 D1 260 A1 H H H A2 H Ph D1 D1 261 A1 H H H A4 H Ph D1 D1262 A1 H H H A6 H Ph D1 D1 263 A1 H H H A9 H Ph D1 D1 264 H A1 A2 H H D1D1 D1 D1 265 H A1 A4 H H D1 D1 D1 D1 266 H A1 A6 H H D1 D1 D1 D1 267 HA1 A9 H H D1 D1 D1 D1 268 H A1 A2 H H D1 Ph D1 D1 269 H A1 A4 H H D1 PhD1 D1 270 H A1 A6 H H D1 Ph D1 D1 271 H A1 A9 H H D1 Ph D1 D1 272 A2 A4H H H D1 Ph D1 D1 273 A2 A6 H H H D1 Ph D1 D1 274 A2 A9 H H H D1 Ph D1D1 275 A4 A6 H H H D1 Ph D1 D1 276 A4 A9 H H H D1 Ph D1 D1 277 A6 A6 H HH D1 Ph D1 D1 278 A6 A9 H H H D1 Ph D1 D1 279 H A2 A4 H H D1 Ph D1 D1280 H A2 A6 H H D1 Ph D1 D1 281 H A2 A9 H H D1 Ph D1 D1 282 H A4 A6 H HD1 Ph D1 D1 283 H A4 A9 H H D1 Ph D1 D1 284 H A6 A6 H H D1 Ph D1 D1 285H A6 A9 H H D1 Ph D1 D1 286 A2 A4 H H H H D1 D1 H 287 A2 A6 H H H H D1D1 H 288 A2 A9 H H H H D1 D1 H 289 A4 A6 H H H H D1 D1 H 290 A4 A9 H H HH D1 D1 H 291 A6 A6 H H H H D1 D1 H 292 A6 A9 H H H H D1 D1 H 293 H A2A4 H H H D1 D1 H 294 H A2 A6 H H H D1 D1 H 295 H A2 A9 H H H D1 D1 H 296H A4 A6 H H H D1 D1 H 297 H A4 A9 H H H D1 D1 H 298 H A6 A6 H H H D1 D1H 299 H A6 A9 H H H D1 D1 H 300 A2 A4 H H H H D1 Ph D1 301 A2 A6 H H H HD1 Ph D1 302 A2 A9 H H H H D1 Ph D1 303 A4 A6 H H H H D1 Ph D1 304 A4 A9H H H H D1 Ph D1 305 A6 A6 H H H H D1 Ph D1 306 A6 A9 H H H H D1 Ph D1307 H A2 A4 H H H D1 Ph D1 308 H A2 A6 H H H D1 Ph D1 309 H A2 A9 H H HD1 Ph D1 310 H A4 A6 H H H D1 Ph D1 311 H A4 A9 H H H D1 Ph D1 312 H A6A6 H H H D1 Ph D1 313 H A6 A9 H H H D1 Ph D1 314 H A1 H A1 H D1 D1 D1 D1315 H A1 H A1 H D2 D2 D2 D2 316 H A1 H A1 H D3 D3 D3 D3 317 H A1 H A1 HD4 D4 D4 D4 318 H A1 H A1 H D5 D5 D5 D5 319 H A1 H A1 H D6 D6 D6 D6 320H A1 H A1 H D11 D11 D11 D11 321 H A1 H A1 H D4 D1 D4 D4 322 H A1 H A1 HD1 D4 D4 D4 323 H A1 H A1 H D1 D4 D4 D1 324 H A1 H A1 H D4 D1 D1 D4 325H A1 H A1 H D1 D1 Ph D1 326 H A1 H A1 H D2 D2 Ph D2 327 H A1 H A1 H D3D3 Ph D3 328 H A1 H A1 H D4 D4 Ph D4 329 H A1 H A1 H D1 D11 Ph D1 330 HA1 H A1 H D1 D5 Ph D1 331 H A1 H A1 H D1 D11 Ph D1 332 H A1 H A1 H D11D1 Ph D11 333 H A1 H A1 H D11 D11 Ph D11 334 H A1 H A1 H D5 D5 Ph D5 335H A1 H A1 H H D5 Ph D5 336 H A1 H A1 H H D1 D1 D11 337 H A1 H A1 H H D1D1 D1 338 H A1 H A1 H H D1 D1 D4 339 H A1 H A1 H H D1 D1 D5 340 H A1 HA1 H H D1 D1 H 341 H A1 H A1 H H D11 D11 H 342 H A1 H A1 H H D11 Ph D11343 H A1 H A1 H H D1 Ph D1 344 H A1 H A1 H H D5 Ph D5 345 H A1 H A1 H HD11 D11 D1 346 H A1 H A1 H H D11 D11 D11 347 H A1 H A1 H H D3 D3 H 348 HA1 H A1 H H D4 D4 H 349 H A1 H A1 H H D5 D5 H 350 H A1 H A1 H H D4 D4 D1351 H A1 H A1 H H D5 D5 D1 352 H A1 H A1 H H D5 D5 D5 353 H A1 H A1 H D4Ph D1 D4 354 H A1 H A1 H D1 Ph D1 D1 355 H A1 H A1 H D1 Ph D11 D1 356 HA1 H A1 H D1 Ph D4 D1 357 H A1 H A1 H D1 Ph D5 D1 358 H A1 H A1 H D11 PhD1 D11 359 H A1 H A1 H D11 Ph D11 D11 360 H A1 H A1 H D3 D3 Ph D3 361 HA1 H A1 H D4 Ph D1 D4 362 H A1 H A1 H D5 D1 Ph D5 363 H A1 H A1 H H D1D1 D1 364 H A1 H A1 H H D1 D1 D11 365 H A1 H A1 H H D1 D1 D4 366 H A1 HA1 H H D1 D1 D5 367 H A1 H A1 H H D1 D1 H 368 H A1 H A1 H H D1 Ph D1 369H A1 H A1 H H D11 D11 D1 370 H A1 H A1 H H D11 D11 D11 371 H A1 H A1 H HD11 D11 H 372 H A1 H A1 H H D11 Ph D11 373 H A1 H A1 H H D3 D3 D3 374 HA1 H A1 H H D3 D3 H 375 H A1 H A1 H H D4 D4 D1 376 H A1 H A1 H H D4 D4 H377 H A1 H A1 H H D5 D5 D1 378 H A1 H A1 H H D5 D5 H 379 H A1 H A1 H HD6 D6 H 380 H A1 H A1 H H D22 D22 H 381 H A1 H A1 H H D52 D62 H 382 H A1H A1 H H D60 D60 H 383 H A1 H A1 H H D70 D70 H 384 H A1 H A1 H Ph D1 D1Ph 385 H A1 H A1 H Ph D5 D5 Ph 386 H A1 H A1 H D5 D11 Ph D5 387 H A1 HA1 H D7 D7 D7 D7 388 H A1 H A1 H D8 D8 D8 D8 389 H A1 H A1 H D9 D9 D9 D9390 H A1 H A1 H D10 D10 D10 D10 391 H A1 H A1 H D3 D1 Ph D3

In some embodiments, the compound of Formula (I) is selected from

3-(2,5-bis(3-(4-(9H-carbazol-9-yl)phenyl)-9H-carbazol-9-yl)-3,6-diphenylpyridin-4-yl)phthalonitrile,3-(2,5-bis(3-(4-(9H-carbazol-9-yl)phenyl)-9H-carbazol-9-yl)-3,6-diphenylpyridin-4-yl)phthalonitrile,9,9′,9″-(4-(2,3-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-5-phenylpyridine-2,3,6-triyl)tris(3-methyl-9H-carbazole),3-(2,5-di(9H-carbazol-9-yl)-3,6-diphenylpyridin-4-yl)phthalonitrile,3-(2,3,5-tris(3,6-dimethyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,3-(3,5-bis(4-(3-(4-(9H-carbazol-9-yl)phenyl)-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,3-(2,3,5-tris(3-phenyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,3-(2,3,6-tris(3-(tert-butyl)-9H-carbazol-9-yl)-5-phenylpyridin-4-yl)phthalonitrile,9,9′,9″-(4-(2,3-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,6-triyl)tris(3-(tert-butyl)-9H-carbazole,3-(3-phenyl-2,5,6-tris(3-phenyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,3-(2,6-bis(3,6-diphenyl-9H-carbazol-9-yl)-3,5-diphenylpyridin-4-yl)phthalonitrile,3-(2,6-diphenyl-3,5-bis(3-phenyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,3-(2,6-bis(3-phenyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,3-(2,6-bis(4-(3-phenyl-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,9,9′-(4-(2,3-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,5-diyl)bis(3,6-diphenyl-9H-carbazole),9,9′,9″-(4-(2,3-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,5-triyl)tris(3,6-dimethyl-9H-carbazole),3-(2,3,6-tris(3,6-dimethyl-9H-carbazol-9-yl)-5-phenylpyridin-4-yl)phthalonitrile,3-(2,5-bis(2-(3,6-diphenyl-9H-carbazol-9-yl)phenyl)-3,6-diphenylpyridin-4-yl)phthalonitrile,3-(3,5-bis(4-(3-(4-(diphenylamino)phenyl)-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,3-(2,3,6-tris(3-methyl-9H-carbazol-9-yl)-5-phenylpyridin-4-yl)phthalonitrile,3-(2,6-bis(4-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,3-(2,6-bis(3-(4-(9H-carbazol-9-yl)phenyl)-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,3-(2,5-bis(4-(3-(4-(diphenylamino)phenyl)-9H-carbazol-yl)phenyl)pyridin-4-yl)phthalonitrile,9,9′-(4-(2,3-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,6-diyl)bis(3-methyl-9H-carbazole),3-(3,5-bis(3-methyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,3-(2,5-di(9H-[3,9′-bicarbazol]-9-yl)pyridin-4-yl)phthalonitrile,3-(2,3,6-tri(9H-[3,9′-bicarbazol]-9-yl)pyridin-4-yl)phthalonitrile,3-(2,5-bis(3,6-di-tert-butyl-9H-carbazol-9-yl)-3,6-diphenylpyridin-4-yl)phthalonitrile,9,9′,9″-(4-(2,3-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,6-triyl)tris(3,6-dimethyl-9H-carbazole),3-(2,5-bis(3-(4-(9H-carbazol-9-yl)phenyl)-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile3-(2,6-bis(3-methyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,3-(2,3,5,6-tetra(9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,3-(2,6-bis(5H-pyrido[3,2-b]indol-5-yl)pyridin-4-yl)phthalonitrile,3-(2,5-bis(3-(4-(diphenylamino)phenyl)-9H-carbazol-9-yl)-3,6-diphenylpyridin-4-yl)phthalonitrile,3-(2,6-bis(4-(9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,3-(2,3,5-tris(3-(tert-butyl)-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,3-(2,6-bis(4-(3-(tert-butyl)-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,3-(2,5-bis(3-(tert-butyl)-9H-carbazol-9-yl)-3,6-diphenylpyridin-4-yl)phthalonitrile,3-(2,6-di(9′H-[9,3′:6′,9″-tercarbazol]-9′-yl)pyridin-4-yl)phthalonitrile,3-(2,3,6-tris(3,6-di-tert-butyl-9H-carbazol-9-yl)-5-phenylpyridin-4-yl)phthalonitrile,3-(2,6-bis(4-(3,6-diphenyl-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,3-(3,5-bis(3-phenyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,3-(2,3,5,6-tetrakis(3-(tert-butyl)-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,3-(2,6-bis(4-(3-(4-(diphenylamino)phenyl)-9H-carbazol-9-yl)-phenyl)pyridin-4-yl)phthalonitrile,3-(2-phenyl-3,5,6-tris(3-phenyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile3-(2,6-di(9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,3-(2,6-bis(4-(3,6-dimethyl-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,3-(2,3,5-tris(3-(tert-butyl)-9H-carbazol-9-yl)-6-phenylpyridin-4-yl)phthalonitrile,3-(3,5-bis(3,6-diphenyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,3-(2,6-di(9H-[3,9′-bicarbazol]-9-yl)pyridin-4-yl)phthalonitrile,3-(2,3,5,6-tetrakis(3-methyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,3-(2,6-bis(3-(tert-butyl)-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,9,9′-(4-(2,3-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,6-diyl)bis(3,6-dimethyl-9H-carbazole),3-(3,5-bis(4-(3-(tert-butyl)-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,3-(3,5-bis(3-(tert-butyl)-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,3-(2,5-bis(3-(4-(diphenylamino)phenyl)-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,9,9′-(4-(2,3-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,6-diyl)bis(3-(tert-butyl)-9H-carbazole),3-(2,5-bis(2-(3,6-diphenyl-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,3-(3,5-bis(3,6-di-tert-butyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,3-(2,5-di(9′H-[9,3′:6′,9″-tercarbazol]-9′-yl)pyridin-4-yl)phthalonitrile,3-(2,6-bis(3,6-di-tert-butyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,3-(2,3,5-tris(3,6-di-tert-butyl-9H-carbazol-9-yl)-6-phenylpyridin-4-yl)phthalonitrile,9′,9″″-(4-(2,3-di(pyridin-4-yl)phenyl)pyridine-3,5-diyl)bis(9′H-9,3′:6′,9″-tercarbazole),3-(2,3,5-tris(3,6-diphenyl-9H-carbazol-9-yl)-6-phenylpyridin-4-yl)phthalonitrile,3-(2,6-bis(9H-pyrido[3,4-b]indol-9-yl)pyridin-4-yl)phthalonitrile,3-(2,3,5,6-tetrakis(3-phenyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,9,9′,9″-(4-(2,3-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,5-triyl)tris(3-(tert-butyl)-9H-carbazole),3-(2,3,6-tri(9H-carbazol-9-yl)-5-phenylpyridin-4-yl)phthalonitrile,3-(2,3,5-tris(3,6-di-tert-butyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,3-(2,6-bis(3,6-dimethyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,3-(2,5-bis(3,6-diphenyl-9H-carbazol-9-yl)-3,6-diphenylpyridin-4-yl)phthalonitrile,9,9′,9″-(4-(2,3-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,6-triyl)tris(3,6-dimethyl-9H-carbazole),3-(2,3,5,6-tetrakis(3,6-dimethyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,3-(2,3,5-tri(9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,9-9′-(4-(2,3-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,6-diyl)bis(3,6-di-tert-butyl-9H-carbazole),9,9′,9″-(2,3-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-5-phenylpyridine-2,3,6-triyl)tris(3,6-dimethyl-9H-carbazole),3-(2,6-bis(3,6-diphenyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,3-(2,3,5-tris(3,6-diphenyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,3-(3,5-di(9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,3-(2,3,5-tris(3-methyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,3-(2,6-bis(3-(4-(diphenylamino)phenyl)-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,3-(2,5-diphenyl-3,6-bis(3-phenyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,3-(3,5-bis(3,6-dimethyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,9,9′-(4-(2,3-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,5-diyl)bis(3,6-dimethyl-9H-carbazole),9,9′(4-(2,3-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-3,5-diyl)bis(3,6-dimethyl-9H-carbazole),and3-(2,3,6-tri(9H-[3,9′-bicarbazol]-9-yl)-5-phenylpyridin-4-yl)phthalonitrile.

In some embodiments, the compound of Formula (I) is selected from

In some embodiments, the compound of Formula (I) is selected from

In some embodiments, the compound of Formula (I) is

In some embodiments, the compound of Formula (II) is selected from

4-(3,5-bis(3-(4-(diphenylamino)phenyl)-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,9,9′,9″-(4-(3,4-di(pyridin-4-yl)phenyl)pyridine-2,3,5-triyl)tris(9H-3,9′-bicarbazole),4-(2,6-di(9H-[3,9′-bicarbazol]-9-yl)-3,5-diphenylpyridin-4-yl)phthalonitrile,4-(2,5-bis(2-(3-(tert-butyl)-9H-carbazol-9-yl)phenyl)-3,6-diphenylpyridin-4-yl)phthalonitrile,4-(2,6-bis(3-(4-(diphenylamino)phenyl)-9H-carbazol-9-yl)-3,5-diphenylpyridin-4-yl)phthalonitrile,4-(3,5-bis(2-(3-methyl-9H-carbazol-9-yl)phenyl)-2,6-diphenylpyridin-4-yl)phthalonitrile,4-(2,5-bis(3,6-diphenyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,4-(2,5-bis(3-(4-(diphenylamino)phenyl)-9H-carbazol-9-yl)-3,6-diphenylpyridin-4-yl)phthalonitrile,4-(3-phenyl-2,5,6-tris(3-phenyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,9′,9″″-(4-(3,4-di(pyridin-3-yl)phenyl)pyridine-2,6-diyl)bis(9′H-9,3′:6′,9″-tercarbazole)4-(2,6-di(9′H-[9,3′:6′,9″-tercarbazol]-9′-yl)pyridin-4-yl)phthalonitrile,4-(3,5-bis(3,6-diphenyl-9H-carbazol-9-yl)-2,6-diphenylpyridin-4-yl)phthalonitrile,9,9″-(4-(3,4-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,5-diyl)bis((9H-3,9′-bicarbazole)),4-(2,5-bis(3-phenyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,9,9′-(4-(3,4-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,6-diyl)bis(3-(tert-butyl)-9H-carbazole),4-(2,5-bis(3-(4-(9H-carbazol-9-yl)phenyl)-9H-carbazol-9-yl)-3,6-diphenylpyridin-4-yl)phthalonitrile,9,9′-(4-(3,4-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,6-diyl)bis(3-phenyl-9H-carbazole),4-(3,5-bis(2-(3,6-diphenyl-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,4-(2,3,5,6-tetrakis(2-(3,6-dimethyl-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,4-(2,6-bis(3-(4-(9H-carbazol-9-yl)phenyl)-9H-carbazol-9-yl)-3,5-diphenylpyridin-4-yl)phthalonitrile,4-(3,5-bis(3,6-dimethyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,9,9″-(4-(3,4-di(pyridin-4-yl)phenyl)pyridine-2,6-diyl)bis(9H-3,9′-bicarbazole),9,9′,9″-(4-(3,4-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,6-triyl)tris(3,6-dimethyl-9H-carbazole),4-(2,3,5-tri(9H-[3,9′-bicarbazol]-9-yl)-6-phenylpyridin-4-yl)phthalonitrile,4-(3,5-bis(3-(tert-butyl)-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,4-(2,3,5,6-tetrakis(2-(3-methyl-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,4-(2-phenyl-3,5,6-tris(3-phenyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,4-(3,5-bis(4-(3,6-diphenyl-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,4-(3,5-bis(3-methyl-9H-carbazol-9-yl)pyridin-4-yl)-phthalonitrile,4-(3,5-bis(3,6-diphenyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,4-(2,3,6-tris(4-(3,6-dimethyl-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,4-(3,5-bis(2-(3,6-diphenyl-9H-carbazol-9-yl)phenyl)-2,6-diphenylpyridin-4-yl)phthalonitrile,4-(2,3,6-tri(9H-[3,9′-bicarbazol]-9-yl)pyridin-4-yl)phthalonitrile,4-(2,5-diphenyl-3,6-bis(3-phenyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,4-(3,5-bis(4-(3-(4-(diphenylamino)phenyl)-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,9,9′,9″-(4-(3,4-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-5-phenylpyridine-2,3,6-triyl)tris(3,6-dimethyl-9H-carbazole),4-(2,3,6-tri(9H-[3,9′-bicarbazol]-9-yl)-5-phenylpyridin-4-yl)phthalonitrile,4-(2,5-bis(4-(3-(4-(diphenylamino)phenyl)-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,4-(2,6-bis(4-(3-(4-(9H-carbazol-9-yl)phenyl)-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,9,9′,9″-(4-(3,4-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,6-triyl)tris(3-methyl-9H-carbazole),9,9′-(4-(3,4-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,5-diyl)bis(3,6-diphenyl-9H-carbazole),9,9′-(4-(3,4-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,5-diyl)bis(3-(tert-butyl)-9H-carbazole),4-(2,5-bis(4-(9H-[3,9′-bicarbazol]-9-yl)phenyl)pyridin-4-yl)phthalonitrile,4-(2,6-bis(2-(3-(4-(9H-carbazol-9-yl)phenyl)-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,4-(2,6-bis(3-methyl-9H-carbazol-9-yl)-3,5-diphenylpyridin-4-yl)phthalonitrile,4-(2,5-bis(3,6-dimethyl-9H-carbazol-9-yl)-3,6-diphenylpyridin-4-yl)phthalonitrile,4-(3,5-bis(3-(9H-carbazol-9-yl)phenyl)-2,6-diphenylpyridin-4-yl)phthalonitrile,4,4′-((4-(3,4-di(pyridin-3-yl)phenylpyridine-2,6-diyl)bis(9H-carbazole-9,3-diyl))bis(N,N-diphenylaniline),4-(3,5-bis(2-(3-methyl-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,4-(2,5-di(10H-phenoxazin-10-yl)-3,6-diphenylpyridin-4-yl)phthalonitrile,4-(2,5-bis(3-methyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,4-(2,6-bis(3-(4-(diphenylamino)phenyl)-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,4-(2,5-bis(3-(tert-butyl)-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,4-(2,6-bis(3,6-di-tert-butyl-9H-carbazol-9-yl)-3,5-diphenylpyridin-4-yl)phthalonitrile,4-(2,5-bis(3-(4-(9H-carbazol-9-yl)phenyl)-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,9,9″-(4-(3,4-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,6-diyl)bis((9H-3,9′-bicarbazole)),4-(2,3,5-tris(3-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,4-(2,6-bis(3-(tert-butyl)-9H-carbazol-9-yl)-3,5-diphenylpyridin-4-yl)phthalonitrile,9′,9″″(4-(3,4-di(pyridin-4-yl)phenyl)pyridine-2,6-diyl)bis(9′H-9,3′:6′,9″-tercarbazole),4-(2,3,6-tri(10H-phenoxazin-10-yl)-5-phenylpyridin-4-yl)phthalonitrile,9′,9″″-(4-(3,4-di(pyridin-3-yl)phenyl)pyridine-2,5-diyl)bis(9′H-9,3′:6′,9″-tercarbazole),4-(2,3,5-tris(3,6-di-tert-butyl-9H-carbazol-9-yl)-6-phenylpyridin-4-yl)phthalonitrile,4-(2,6-bis(11H-benzo[a]carbazol-11-yl)-3,5-diphenylpyridin-4-yl)phthalonitrile,4-(2,6-bis(4-(9H-[3,9′-bicarbazol]-9-yl)phenyl)pyridin-4-yl)phthalonitrile,4-(2,3,6-tris(3-(tert-butyl)-9H-carbazol-9-yl)-5-phenylpyridin-4-yl)phthalonitrile,4-(2,5-bis(3-(tert-butyl)-9H-carbazol-9-yl)-3,6-diphenylpyridin-4-yl)phthalonitrile,4-(3,5-bis(4-(3-(4-(9H-carbazol-9-yl)phenyl)-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,4-(2,6-bis(3-(3-methyl-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,9,9′,9″(4-(3,4-bis(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,3,6-triyl)tris(3-(tert-butyl)-9H-carbazole),4-(3,5-bis(2-(3,6-dimethyl-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,4-(3,5-bis(3-(3-methyl-9H-carbazol-9-yl)phenyl)-2,6-diphenylpyridin-4-yl)phthalonitrile,9,9′-(4-(3,4-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,6-diyl)bis(3,6-diphenyl-9H-carbazole),4-(3,5-bis(4-(3-(tert-butyl)-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,9,9′-(4-(3,4-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,6-diyl)bis(3,6-di-tert-butyl-9H-carbazole),4-(2,5-di(9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,4-(2,5-bis(3-methyl-9H-carbazol-9-yl)-3,6-diphenylpyridin-4-yl)phthalonitrile,4-(2,5-bis(2-(3-methyl-9H-carbazol-9-yl)phenyl)-3,6-diphenylpyridin-4-yl)phthalonitrile,4-(3,5-di(9H-[3,9′-bicarbazol]-9-yl)-2,6-diphenylpyridin-4-yl)phthalonitrile.4-(2,6-bis(2-(3-methyl-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,4-(3,5-diphenyl-2,6-bis(3-phenyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,4-(3,5-di(10H-phenoxazin-10-yl)-2,6-diphenylpyridin-4-yl)phthalonitrile,4-(2,6-di(9H-[3,9-bicarbazol]-9-yl)pyridin-4-yl)phthalonitrile,4-(2,3,6-tris(9H-pyrido[3,4-b]indol-9-yl)pyridin-4-yl)phthalonitrile,4-(3,5-bis(2-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,4-(3,5-di(9′H-[9,3′:6′,9″-tercarbazol]-9′-yl)pyridin-4-yl)phthalonitrile,4-(3,5-bis(3-methyl-9H-carbazol-9-yl)-2,6-diphenylpyridin-4-yl)phthalonitrile,4-(3,5-bis(4-(3,6-dimethyl-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,9,9″-(4-(3,4-bis(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,5-diyl)bis((9H-3,9′-bicarbazole)),9,9′,9″-(4-(3,4-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,3,6-triyl)tris(3-(tert-butyl)-9H-carbazole),4-(2,3,5-tris(2-(3-methyl-9H-carbazol-9-yl)phenyl)-6-phenylpyridin-4-yl)phthalonitrile,4-(3,5-bis(3,6-dimethyl-9H-carbazol-9-yl)-2,6-diphenylpyridin-4-yl)phthalonitrile,4-(2,5-bis(3,6-diphenyl-9H-carbazol-9-yl)-3,6-diphenylpyridin-4-yl)phthalonitrile,4-(3,5-bis(2-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)-2,6-diphenylpyridin-4-yl)phthalonitrile,4-(3,5-di(9H-carbazol-9-yl)pyridin-4-yl)-phthalonitrile,4-(2,5-bis(3,6-di-tert-butyl-9H-carbazol-9-yl)-3,6-diphenylpyridin-4-yl)phthalonitrile,4-(3,5-bis(2-(3-(tert-butyl)-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,9-9′,9″-(4-(3,4-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-5-phenylpyridine-2,3,6-triyl)tris(3-methyl-9H-carbazole),4-(3,5-bis(3,6-di-tert-butyl-9H-carbazol-9-yl)-2,6-diphenylpyridin-4-yl)phthalonitrile,4-(3,5-bis(3-(tert-butyl)-9H-carbazol-9-yl)-2,6-diphenylpyridin-4-yl)phthalonitrile,9,9′,9″-(4-(3,4-bis(2,6-diphenylpyrimidin-4-yl)phenyl)pyridine-2,3,6-triyl)tris(3-methyl-9H-carbazole),4-(3,5-bis(3-phenyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,4-(2,3,5-tri(9H-carbazol-9-yl)-6-phenylpyridin-4-yl)phthalonitrile,4-(2,6-bis(2-(3,6-diphenyl-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,4-(2,3,5,6-tetrakis(7H-benzo[c]carbazol-7-yl)pyridin-4-yl)phthalonitrile,4-(2,5-bis(4-(3-(4-(9H-carbazol-9-yl)phenyl)-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,4-(3,5-bis(2-(3-(tert-butyl)-9H-carbazol-9-yl)phenyl)-2,6-diphenylpyridin-4-yl)phthalonitrile,4-(2,3,6-tris(3,6-di-tert-butyl-9H-carbazol-9-yl)-5-phenylpyridin-4-yl)phthalonitrile,4-(2,5-di(9′H-[9,3′:6′,9″-tercarbazol]-9′-yl)pyridin-4-yl)phthalonitrile,4-(2,5-bis(3-(4-(diphenylamino)phenyl)-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,4-(2,6-di(9H-carbazol-9-yl)-3,5-diphenylpyridin-4-yl)phthalonitrile,4-(2,6-bis(2-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,4-(2,6-bis(3,6-dimethyl-9H-carbazol-9-yl)-3,5-diphenylpyridin-4-yl)phthalonitrile,4-(2,3,6-tris(3-phenyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,4-(3,5-bis(3-(4-(9H-carbazol-9-yl)phenyl)-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,9,9′-(4-(3,4-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,6-diyl)bis(3-methyl-9H-carbazole),4-(2,3,6-tris(4-(3-phenyl-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,9,9″,9″″-(4-(3,4-di(pyridin-4-yl)phenyl)pyridine-2,3,6-triyl)tris(9H-3,9′-bicarbazole),9,9′-(4-(3,4-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)-3,5-diphenylpyridine-2,6-diyl)bis(3-phenyl-9H-carbazole),4-(2,6-bis(4-(3-(4-(diphenylamino)phenyl)-9H-carbazol-9-yl)phenyl)pyridin-4-yl)phthalonitrile,4-(2,6-diphenyl-3,5-bis(3-phenyl-9H-carbazol-9-yl)pyridin-4-yl)phthalonitrile,4-(2,3,5-tri(9H-[3,9′-bicarbazol]-9-yl)pyridin-4-yl)phthalonitrile,4-(2,6-bis(3,6-diphenyl-9H-carbazol-9-yl)-3,5-diphenylpyridin-4-yl)phthalonitrile,4-(3,5-bis(3-(4-(9H-carbazol-9-yl)phenyl)-9H-carbazol-9-y)-2,6-diphenylpyridin-4-yl)phthalonitrile,and9,9′-(4-(3,4-bis(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)pyridine-2,5-diyl)bis(3,6-di-tert-butyl-9H-carbazole).

In some embodiments, the compound of Formula (II) is selected from

In some embodiments, the compound of Formula (II) is selected from

In some embodiments, the compound of Formula (II) is

In some embodiments, compounds of Formula (I) are substituted with atleast one deuterium.

In some embodiments, compounds of Formula (I) are light-emittingmaterials.

In some embodiments, compounds of Formula (I) are compound capable ofemitting delayed fluorescence.

In some embodiments, compounds of Formula (I) are light-emittingmaterials.

In some embodiments, compounds of Formula (I) are assist dopantmaterials.

In some embodiments of the present disclosure, when excited via thermalor electronic means, the compounds of Formula (I) can produce light inUV region, the blue, green, yellow, orange, or red region of the visiblespectrum (e.g., about 420 nm to about 500 nm, about 500 nm to about 600nm, or about 600 nm to about 700 nm), or near-IR region.

In some embodiments of the present disclosure, when excited via thermalor electronic means, the compounds of Formula (I) can produce light inthe red or orange region of the visible spectrum (e.g., about 620 nm toabout 780 nm; about 650 nm).

In some embodiments of the present disclosure, when excited via thermalor electronic means, the compounds of Formula (I) can produce light inthe orange or yellow region of the visible spectrum (e.g., about 570 nmto about 620 nm; about 590 nm; about 570 nm).

In some embodiments of the present disclosure, when excited via thermalor electronic means, the compounds of Formula (I) can produce light inthe green region of the visible spectrum (e.g., about 490 nm to about575 nm; about 510 nm).

In some embodiments of the present disclosure, when excited via thermalor electronic means, the compounds of Formula (I) can produce light inthe blue region of the visible spectrum (e.g., about 400 nm to about 490nm; about 475 nm).

Electronic properties of a library of small chemical molecules can becomputed using known ab initio quantum mechanical computations. Forexample, using a time-dependent density functional theory using, as abasis set, the set of functions known as 6-31G* and a Becke,3-parameter, Lee-Yang-Parr hybrid functional to solve Hartree-Fockequations (TD-DFT/B3LYP/6-31G*), molecular fragments (moieties) can bescreened which have HOMOs above a specific threshold and LUMOs below aspecific threshold, and wherein the calculated triplet state of themoieties is above 2.75 eV.

Therefore, for example, a donor moiety can be selected because it has aHOMO energy (e.g., an ionization potential) of greater than or equal to−6.5 eV. An acceptor moiety (“A”) can be selected because it has, forexample, a LUMO energy (e.g., an electron affinity) of less than orequal to −0.5 eV. The bridge moiety (“B”) can be a rigid conjugatedsystem that can, for example, sterically restrict the acceptor and donormoieties into a specific configuration, thereby preventing the overlapbetween the conjugated π system of donor and acceptor moieties.

In some embodiments, the compound library is filtered using one or moreof the following properties

-   -   1. emission near a certain wavelength;    -   2. calculated triplet state above a certain energy level;    -   3. ΔE_(ST) value below a certain value;    -   4. quantum yield above a certain value;    -   5. HOMO level; and    -   6. LUMO level.

some embodiments, the difference between the lowest singlet excitedstate and the lowest triplet excited state at 77K (ΔE_(ST)) is less thanabout 0.5 eV, less than about 0.4 eV, less than about 0.3 eV, less thanabout 0.2 eV, or less than about 0.1 eV. In some embodiments, theΔE_(ST) value is less than about 0.09 eV, less than about 0.08 eV, lessthan about 0.07 eV, less than about 0.06 eV, less than about 0.05 eV,less than about 0.04 eV, less than about 0.03 eV, less than about 0.02eV, or less than about 0.01 eV.

In some embodiments, a compound of Formula (I) exhibits a quantum yieldof greater than 25%, such as about 30%, about 35%, about 40%, about 45%,about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about80%, about 85%, about 90%, about 95%, or greater.

Preparation of the Disclosed Compounds

The compounds of Formula (I) can be synthesized by any method known toone of ordinary skills in the art. The compounds are synthesized fromthe commonly available starting material. In some embodiments, thecompounds of Formula (I) are synthesized by reacting a precursor ofFormula (III) and a compound of Formula (IV).

In Formula (III), R¹, R², R³ and R⁴ are as defined in R¹, R², R³ and R⁴of Formula (I), and X is halogen. In Formula (IV), Z¹, Z², Z³, Z⁴ and Z⁵are as defined in Z¹, Z², Z³, Z⁴ and Z⁵ of Formula (I).

The known reaction conditions can be appropriately selected and used.For the details of the reaction, reference may be made to the synthesisexamples described later (see Example 2).

In some embodiments, the compounds of Formula (III) have a structure ofFormula (IIIa):

wherein X is halogen, and D¹, D², D³ and D⁴ are independently D.

In some embodiments, X is fluorine. In some embodiments, X is chlorine.In some embodiments, X is bromine. In some embodiments, X is iodine.

D is as defined in Formula (I). In some embodiments, at least one of D¹,D², D³ and D⁴ is a group of Formula (IIa). In some embodiments, at leastone of D¹, D², D³ and D⁴ is a group of Formula (IIb). In someembodiments, at least one of D¹, D², D³ and D⁴ is a group of Formula(IIc). In some embodiments, at least one of D¹, D², D³ and D⁴ is a groupof Formula (IId). In some embodiments, at least two of D¹, D², D³ and D⁴are independently a group of Formula (IIa). In some embodiments, atleast two of D¹, D², D³ and D⁴ are independently a group of Formula(IIb). In some embodiments, at least two of D¹, D², D³ and D⁴ areindependently a group of Formula (IIc). In some embodiments, at leasttwo of D¹, D², D³ and D⁴ are independently a group of Formula (IId). Insome embodiments, D¹, D², D³ and D⁴ are independently a group of Formula(IIa). In some embodiments, D¹, D², D³ and D⁴ are independently a groupof Formula (IIb). In some embodiments, D¹, D², D³ and D⁴ areindependently a group of Formula (IIc). In some embodiments, D¹, D², D³and D⁴ are independently a group of Formula (IId).

In some embodiments, D¹ and D² are the same, and D³ and D⁴ are differentfrom D¹ and D². In some embodiments, D¹ and D³ are the same, and D² andD⁴ are different from D¹ and D⁴. In some embodiments, D¹ and D⁴ are thesame, and D² and D³ are different from D¹ and D⁴. In some embodiments,D² and D³ are the same, and D¹ and D⁴ are different from D² and D³. Insome embodiments, D¹, D² and D³ are the same and D⁴ is different. Insome embodiments, D¹, D² and D⁴ are the same and D³ is different. Insome embodiments, D¹, D², D³ and D⁴ are the same.

In some embodiments, the compound of Formula (IIIa) is selected fromCompounds 1001 to 1102 shown in the following tables:

X D¹ D² D³ D⁴ 1001 Br D1 D1 D1 D1 1002 Br D2 D2 D2 D2 1003 Br D3 D3 D3D3 1004 Br D4 D4 D4 D4 1005 Br D5 D5 D5 D5 1006 Br D6 D6 D6 D6 1007 BrD7 D7 D7 D7 1008 Br D8 D8 D8 D8 1009 Br D9 D9 D9 D9 1010 Br D10 D10 D10D10 1011 Br D11 D11 D11 D11 1012 Br D21 D21 D21 D21 1013 Br D22 D22 D22D22 1014 Br D52 D52 D52 D52 1015 Br D60 D60 D60 D60 1016 Br D72 D72 D72D72 1017 F D1 D1 D1 D1 1018 F D2 D2 D2 D2 1019 F D3 D3 D3 D3 1020 F D4D4 D4 D4 1021 F D5 D5 D5 D5 1022 F D6 D6 D6 D6 1023 F D7 D7 D7 D7 1024 FD8 D8 D8 D8 1025 F D9 D9 D9 D9 1026 F D10 D10 D10 D10 1027 F D11 D11 D11D11 1028 F D21 D21 D21 D21 1029 F D22 D22 D22 D22 1030 F D52 D52 D52 D521031 F D60 D60 D60 D60 1032 F D72 D72 D72 D72 1033 Cl D1 D1 D1 D1 1034Cl D2 D2 D2 D2 1035 Cl D3 D3 D3 D3 1036 Cl D4 D4 D4 D4 1037 Cl D5 D5 D5D5 1038 Cl D6 D6 D6 D6 1039 Cl D7 D7 D7 D7 1040 Cl D8 D8 D8 D8 1041 ClD9 D9 D9 D9 1042 Cl D10 D10 D10 D10 1043 Cl D11 D11 D11 D11 1044 Cl D21D21 D21 D21 1045 Cl D22 D22 D22 D22 1046 Cl D52 D52 D52 D52 1047 Cl D60D60 D60 D60 1048 Cl D72 D72 D72 D72 1049 I D1 D1 D1 D1 1050 I D2 D2 D2D2 1051 I D3 D3 D3 D3 1052 I D4 D4 D4 D4 1053 I D5 D5 D5 D5 1054 I D6 D6D6 D6 1055 I D7 D7 D7 D7 1056 I D8 D8 D8 D8 1057 I D9 D9 D9 D9 1058 ID10 D10 D10 D10 1059 I D11 D11 D11 D11 1060 I D21 D21 D21 D21 1061 I D22D22 D22 D22 1062 I D52 D52 D52 D52 1063 I D60 D60 D60 D60 1064 I D72 D72D72 D72 1065 Br D1 D1 Ph D1 1066 Br D2 D2 Ph D2 1067 Br D3 D3 Ph D3 1068Br D4 D4 Ph D4 1069 Br D1 D11 Ph D1 1070 Br D1 D5 Ph D1 1071 Br D11 D1Ph D11 1072 Br D11 D11 Ph D11 1073 Br D5 D5 Ph D5 1074 Br H D5 Ph D51075 Br H D1 D1 D11 1076 Br H D1 D1 D1 1077 Br H D1 D1 D4 1078 Br H D1D1 D5 1079 Br H D1 D1 H 1080 Br H D11 D11 H 1081 Br H D11 Ph D11 1082 BrH D1 Ph D1 1083 Br H D11 D11 D1 1084 Br H D11 D11 D11 1085 Br H D3 D3 H1086 Br H D4 D4 H 1087 Br H D5 D5 H 1088 Br H D4 D4 D1 1089 Br H D5 D5D1 1090 Br H D5 D5 D5 1091 Br D1 Ph D4 D1 1092 Br D3 D3 Ph D3 1093 Br D4Ph D1 D4 1094 Br D5 D1 Ph D5 1095 Br H D3 D3 D3 1096 Br H D6 D6 H 1097Br H D22 D22 H 1098 Br H D52 D62 H 1099 Br H D60 D60 H 1100 Br H D70 D70H 1101 Br Ph D1 D5 Ph 1102 Br Ph D5 D5 Ph

Compositions with the Disclosed Compounds

In some embodiments, a compound of Formula (I) is combined with,dispersed within, covalently bonded to, coated with, formed on, orotherwise associated with, one or more materials (e.g., small molecules,polymers, metals, metal complexes, etc.) to form a film or layer insolid state. For example, the compound of Formula (I) may be combinedwith an electroactive material to form a film. In some cases, thecompound of Formula (I) may be combined with a hole-transport polymer.In some cases, the compound of Formula (I) may be combined with anelectron-transport polymer. In some cases, the compound of Formula (I)may be combined with a hole-transport polymer and an electron-transportpolymer. In some cases, the compound of Formula (I) may be combined witha copolymer comprising both hole-transport portions andelectron-transport portions. In such embodiments, electrons and/or holesformed within the solid film or layer may interact with the compound ofFormula (I).

Film Formation

In some embodiments, a film containing a compound of the presentinvention of Formula (I) can be formed in a wet process. In a wetprocess, a solution prepared by dissolving a composition containing acompound of the present invention is applied to a surface and formedinto a film thereon after solvent removal. A wet process includes,though not limited thereto, a spin coating method, a slit coatingmethod, a spraying method, an inkjet method (a spay method), a gravureprinting method, an offset printing method, and a flexographic printingmethod. In a wet process, a suitable organic solvent capable ofdissolving a composition containing a compound of the present inventionis selected and used. In some embodiments, a substituent (for example,an alkyl group) capable of increasing solubility in an organic solventcan be introduced into the compound contained in the composition.

In some embodiments, a film containing a compound of the presentinvention can be formed in a dry process. In some embodiments, a dryprocess includes a vacuum evaporation method, but is not limitedthereto. In the case of employing a vacuum evaporation method, compoundsto constitute a film can be vapor-co-deposited from individualevaporation sources, or can be vapor-co-deposited from a singleevaporation source of a mixture of the compounds. In the case of using asingle evaporation source, a mixed powder prepared by mixing powders ofcompounds may be used, or a compression-molded body prepared bycompressing the mixed powder may be used, or a mixture prepared byheating, melting and cooling compounds may be used. In some embodimentswhere vapor-co-deposition is carried out under such a condition that theevaporation rate (weight reduction rate) of the plural compoundscontained in a single evaporation source is the same or is nearly thesame as each other, a film whose composition ratio corresponds to thecomposition ratio of the plural compounds contained in the evaporationsource can be formed. Under the condition where plural compounds aremixed to make an evaporation source in a composition ratio that is thesame as the composition ratio of the film to be formed, a film having adesired composition ratio can be formed in a simplified manner. In someembodiments where a temperature at which the compounds to bevapor-co-deposited could have the same weight reduction ratio isidentified, and the temperature can be employed as the temperature invapor-co-deposition.

Exemplary Uses of the Disclosed Compounds Organic Light-Emitting Diodes

One aspect of the invention relates to use of the compound of Formula(I) of the invention as a light-emitting material of an organiclight-emitting device. In some embodiments, the compound represented byFormula (I) of the invention may be effectively used as a light-emittingmaterial in a light-emitting layer of an organic light-emitting device.In some embodiments, the compound of Formula (I) comprises a delayedfluorescent material emitting delayed fluorescent light (delayedfluorescence emitter). In some embodiments, the invention provides adelayed fluorescence emitter having the structure of Formula (I). Insome embodiments, the invention relates to the use of the compound ofFormula (I) as the delayed fluorescence emitter. In some embodiments,the compound of Formula (I) can be used as a host material and used withone or more light-emitting materials, and the light-emitting materialcan be a fluorescent material, a phosphorescent material or a TADFmaterial. In some embodiments, the compound of Formula (I) can be usedas an assistant dopant and used with one or more light-emittingmaterials and one or more host materials, and the light-emittingmaterial can be a fluorescent material, a phosphorescent material or aTADF material. In some embodiments, the compound of Formula (I) can beused as a hole transport material. In some embodiments, the compound ofFormula (I) can be used as an electron transport material. In someembodiments, the invention relates to a method for emitting delayedfluorescent light from the compound of Formula (I). In some embodiments,an organic light-emitting device comprising the compound as alight-emitting material, emits delayed fluorescent light, and has a highlight emission efficiency.

In some embodiments, a light-emitting layer comprises a compound ofFormula (I), wherein the compound of Formula (I) is oriented parallel tothe substrate. In some embodiments, the substrate is a film formingsurface. In some embodiments, the orientation of the compound of Formula(I) with respect to the film forming surface influences or determinesthe propagation directions of the light emitted by the compound to bealigned. In some embodiments, the alignment of the propagationdirections of the light emitted by the compound of Formula (I) enhancesthe light extraction efficiency from the light-emitting layer.

One aspect of the invention relates to an organic light-emitting device.In some embodiments, the organic light-emitting device comprises alight-emitting layer. In some embodiments, the light-emitting layercomprises a compound of Formula (I) as a light-emitting material. Insome embodiments, the organic light-emitting device is an organicphotoluminescent device (organic PL device). In some embodiments, theorganic light-emitting device is an organic electroluminescent device(organic EL device). In some embodiments, the compound of Formula (I)assists the light emission of another light-emitting material comprisedin the light-emitting layer, i.e., as a so-called assistant dopant. Insome embodiments, the compound of Formula (I) comprised in thelight-emitting layer is in its the lowest excited singlet energy level,which is comprised between the lowest excited singlet energy level ofthe host material comprised in the light-emitting layer and the lowestexcited singlet energy level of the another light-emitting materialcomprised in the light-emitting layer.

In some embodiments, the organic photoluminescent device comprises atleast one light-emitting layer. In some embodiments, the organicelectroluminescent device comprises at least an anode, a cathode, and anorganic layer between the anode and the cathode. In some embodiments,the organic layer comprises at least a light-emitting layer. In someembodiments, the organic layer comprises only a light-emitting layer. Insome embodiments, the organic layer, comprises one or more organiclayers in addition to the light-emitting layer. Examples of the organiclayer include a hole transporting layer, a hole injection layer, anelectron barrier layer, a hole barrier layer, an electron injectionlayer, an electron transporting layer and an exciton barrier layer. Insome embodiments, the hole transporting layer may be a hole injectionand transporting layer having a hole injection function, and theelectron transporting layer may be an electron injection andtransporting layer having an electron injection function. An example ofan organic electroluminescent device is shown in FIG. 1.

In some embodiments, light emission of the organic electroluminescentdevice occurs mainly in the compound of Formula (I). In someembodiments, the organic electroluminescent device is a multiplewavelength light emitting device and the compound of Formula (I) emitslight that has the shortest wavelength.

Substrate

In some embodiments, the organic electroluminescent device of theinvention is supported by a substrate, wherein the substrate is notparticularly limited and may be any of those that have been commonlyused in an organic electroluminescent device, for example those formedof glass, transparent plastics, quartz and silicon.

Anode

In some embodiments, the anode of the organic electroluminescent deviceis made of a metal, an alloy, an electroconductive compound, or acombination thereof. In some embodiments, the metal, alloy, orelectroconductive compound has a large work function (4 eV or more). Insome embodiments, the metal is Au. In some embodiments, theelectroconductive transparent material is selected from CuI, indium tinoxide (ITO), SnO₂, and ZnO. In some embodiments, an amorphous materialcapable of forming a transparent electroconductive film, such as IDIXO(In₂O₃—ZnO), is be used. In some embodiments, the anode is a thin film.In some embodiments the thin film is made by vapor deposition orsputtering. In some embodiments, the film is patterned by aphotolithography method. In some embodiments, where the pattern may notrequire high accuracy (for example, approximately 100 μm or more), thepattern may be formed with a mask having a desired shape on vapordeposition or sputtering of the electrode material. In some embodiments,when a material can be applied as a coating, such as an organicelectroconductive compound, a wet film forming method, such as aprinting method and a coating method is used. In some embodiments, whenthe emitted light goes through the anode, the anode has a transmittanceof more than 10%, and the anode has a sheet resistance of severalhundred Ohm per square or less. In some embodiments, the thickness ofthe anode is from 10 to 1,000 nm. In some embodiments, the thickness ofthe anode is from 10 to 200 nm. In some embodiments, the thickness ofthe anode varies depending on the material used.

Cathode

In some embodiments, the cathode is made of an electrode material ametal having a small work function (4 eV or less) (referred to as anelectron injection metal), an alloy, an electroconductive compound, or acombination thereof. In some embodiments, the electrode material isselected from sodium, a sodium-potassium alloy, magnesium, lithium, amagnesium-copper mixture, a magnesium-silver mixture, amagnesium-aluminum mixture, a magnesium-indium mixture, analuminum-aluminum oxide (Al₂O₃) mixture, indium, a lithium-aluminummixture, and a rare earth metal. In some embodiments, a mixture of anelectron injection metal and a second metal that is a stable metalhaving a larger work function than the electron injection metal is used.In some embodiments, the mixture is selected from a magnesium-silvermixture, a magnesium-aluminum mixture, a magnesium-indium mixture, analuminum-aluminum oxide (Al₂O₃) mixture, a lithium-aluminum mixture, andaluminium. In some embodiments, the mixture increases the electroninjection property and the durability against oxidation. In someembodiments, the cathode is produced by forming the electrode materialinto a thin film by vapor deposition or sputtering. In some embodiments,the cathode has a sheet resistance of several hundred Ohm per square orless. In some embodiments, the thickness of the cathode ranges from 10nm to 5 μm. In some embodiments, the thickness of the cathode rangesfrom 50 to 200 nm. In some embodiments, for transmitting the emittedlight, any one of the anode and the cathode of the organicelectroluminescent device is transparent or translucent. In someembodiments, the transparent or translucent electroluminescent devicesenhances the light emission luminance.

In some embodiments, the cathode is formed with an electroconductivetransparent material, as described for the anode, to form a transparentor translucent cathode. In some embodiments, a device comprises an anodeand a cathode, both being transparent or translucent.

Light-Emitting Layer

In some embodiments, the light-emitting layer is a layer, in which holesand electrons, injected respectively from the anode and the cathode, arerecombined to form excitons. In some embodiments the layer emits light.

In some embodiments, a light-emitting material is solely used as thelight-emitting layer. In some embodiments, the light-emitting layercontains a light-emitting material, and a host material. In someembodiments, the light-emitting material is one or more compounds ofFormula (I). In some embodiments, for the organic electroluminescentdevice and the organic photoluminescent device to exhibit a high lightemission efficiency, the singlet excitons and the triplet excitonsgenerated in the light-emitting material are confined in thelight-emitting material. In some embodiments, a host material is used inaddition to the light-emitting material in the light-emitting layer. Insome embodiments, the host material is an organic compound. In someembodiments, the organic compounds have excited singlet energy andexcited triplet energy, at least one of which is higher than those ofthe light-emitting material of the invention. In some embodiments, thesinglet excitons and the triplet excitons generated in thelight-emitting material of the invention are confined in the moleculesof the light-emitting material of the invention. In some embodiments,the singlet and triplet excitons are sufficiently confined to elicit thelight emission efficiency. In some embodiments, the singlet excitons andthe triplet excitons are not confined sufficiently, though a high lightemission efficiency is still obtained, and thus a host material capableof achieving a high light emission efficiency can be used in theinvention without any particular limitation. In some embodiments, thelight emission occurs in the light-emitting material of thelight-emitting layer in the devices of the invention. In someembodiments, the emitted light contains both fluorescent light anddelayed fluorescent light. In some embodiments, the emitted Sightcomprises emitted light from the host material. In some embodiments, theemitted light consists of emitted light from the host material. In someembodiments, the emitted light comprises emitted light from a compoundof Formula (I), and emitted light from the host material. In someembodiments, a TADF molecule and a host material are used. In someembodiments, the TADF will be assistant dopant.

In some embodiments, when a host material is used, the amount of thecompound of the invention as the light-emitting material contained inthe light-emitting layer is 0.1% by weight or more. In some embodiments,when a host material is used, the amount of the compound of theinvention as the light-emitting material contained in the light-emittinglayer is 1% by weight or more. In some embodiments, when a host materialis used, the amount of the compound of the invention as thelight-emitting material contained in the light-emitting layer is 50% byweight or less. In some embodiments, when a host material is used, theamount of the compound of the invention as the light-emitting materialcontained in the light-emitting layer is 20% by weight or less. In someembodiments, when a host material is used, the amount of the compound ofthe invention as the light-emitting material contained in thelight-emitting layer is 10% by weight or less.

In some embodiments, the host material in the light-emitting layer is anorganic compound comprising a hole transporting function and an electrontransporting function. In some embodiments, the host material in theLight-emitting layer is an organic compound that prevents the emittedlight from being increased in wavelength. In some embodiments, the hostmaterial in the light-emitting layer is an organic compound with a highglass transition temperature.

In some embodiments, a light-emitting layer contains two or more typesof TADF molecules differing in the structure. For example, alight-emitting layer may contain three types of materials of a hostmaterial, a first TADF molecule and a second TADF molecule whose excitedsinglet energy level is higher in that order. In that case, preferably,the first TADF molecule and the second TADF molecule are both such thatthe difference between the lowest excited singlet energy level and thelowest excited triplet energy level at 77 K, ΔE_(ST), is 0.3 eV or less,more preferably 0.25 eV or less, even more preferably 0.2 eV or less,still more preferably 0.15 eV or less, still further more preferably 0.1eV or less, still further more preferably 0.07 eV or less, still furthermore preferably 0.05 eV or less, still further more preferably 0.03 eVor less, and especially further more preferably 0.01 eV or less.Preferably, the content of the first TADF molecule in the light-emittinglayer is larger than the content of the second TADF molecule therein.Also preferably, the content of the host material in the light-emittinglayer is larger than the content of the second TADF molecule therein.The content of the first TADF molecule in the light-emitting layer maybe larger than, or may be smaller than, or may be the same as thecontent of the host material therein. In some embodiments, thecomposition in the light-emitting layer may be such that the hostmaterial is 10 to 70% by weight, the first TADF molecule is 10 to 80% byweight, and the second TADF molecule is 0.1 to 30% by weight. In someembodiments, the composition in the light-emitting layer may be suchthat the host material is 20 to 45% by weight, the first TADF moleculeis 50 to 75% by weight, and the second TADF molecule is 5 to 20% byweight. In some embodiments, the luminescence quantum yield byphotoexcitation, ϕPL1(A), of a vapor-co-deposited film of a first TADFmolecule and a host material (the content of the first TADF molecule inthe vapor-co-deposited film=A% by weight), and the luminescence quantumyield by photoexcitation, ϕPL2(A), of a vapor-co-deposited film of asecond TADF molecule and a host material (the content of the second TADFmolecule in the vapor-co-deposited film=A% by weight) satisfy arelational expression ϕPL1(A)>ϕPL2(A). In some embodiments, theluminescence quantum yield by photoexcitation, ϕPL2(B), of avapor-co-deposited film of a second TADF molecule and a host material(the content of the second TADF molecule in the vapor-co-depositedfilm=B% by weight), and the luminescence quantum yield byphotoexcitation, ϕPL2(100), of a neat film of a second TADF moleculesatisfy a relational expression ϕPL2(B)>ϕPL2(100). In some embodiments,the light-emitting layer may contain three types of TADF moleculesdiffering in the structure. The compound of the present invention may beany of plural TADF compounds contained in the light-emitting layer.

In some embodiments, the light-emitting layer may be composed of amaterial selected from the group consisting of a host material, anassistant dopant and a light-emitting material. In some embodiments, thelight-emitting layer does not contain a metal element. In someembodiments, the light-emitting layer may be formed of a materialcomposed of atoms alone selected from the group consisting of a carbonatom, a hydrogen atom, a nitrogen atom, an oxygen atom and a sulfuratom. Alternatively, the light-emitting layer may be formed of amaterial composed of atoms alone selected from the group consisting of acarbon atom, a hydrogen atom and a nitrogen atom.

When the light-emitting layer contains any other TADF material than thecompound of the present invention, the TADF material may be a knowndelayed fluorescent material. Preferred delayed fluorescent materialsinclude compounds included in general formulae described inWO2013/154064, paragraphs 0008 to 0048 and 0095 to 0133; WO2013/011954,paragraphs 0007 to 0047 and 0073 to 0085; WO2013/011955, paragraphs 0007to 0033 and 0059 to 0066; WO2013/081088, paragraphs 0008 to 0071 and0118 to 0133; JP 2013-256490A, paragraphs 0009 to 0046 and 0093 to 0134;JP 2013-116975A, paragraphs 0008 to 0020 and 0038 to 0040;WO2013/133359, paragraphs 0007 to 0032 and 0079 to 0084; WO2013/161437,paragraphs 0008 to 0054 and 0101 to 0121; JP 2014-9352A, paragraphs 0007to 0041 and 0060 to 0069; JP 2014-9224A, paragraph 0008 to 0048 and 0067to 0076; JP 2017-119663A, paragraphs 0013 to 0025; JP 2017-119664A,paragraphs 0013 to 0026; JP 2017-222623A, paragraphs 0012 to 0025; JP2017-226838A, paragraphs 0010 to 0050; JP 2018-100411A, paragraphs 0012to 0043; WO2018/047853, paragraphs 0016 to 0044; and especiallyexemplified compounds therein capable of emitting delayed fluorescence.Also, light-emitting materials described in JP 2013-253121A,WO2013/133359, WO2014/034535, WO2014/115743, WO2014/122895,WO2014/126200, WO2014/136758, WO2014/133121, WO2014/136860,WO2014/196585, WO2014/189122, WO2014/168101, WO2015-008580,WO2014/203840, WO2015/002213, WO2015/016200, WO2015/019725,WO2015/072470, WO2015/108049, WO2015/080182, WO2015/072537,WO2015/080183, JP 2015-129240A, WO2015/129714, WO2015/129715,WO2015/133501, WO2015/136880, WO2015/137244, WO2015/137202,WO2015/137136, WO2015/146541 and WO2015/159541, and capable of emittingdelayed fluorescence may preferably be employed here. The patentpublications described in this paragraph are herein incorporated byreference as a part of the present disclosure.

Injection Layer

An injection layer is a layer between the electrode and the organiclayer. In some embodiments, the injection layer decreases the drivingvoltage and enhances the light emission luminance. In some embodimentsthe injection layer includes a hole injection layer and an electroninjection layer. The injection layer can be positioned between the anodeand the light-emitting layer or the hole transporting layer, and betweenthe cathode and the light-emitting layer or the electron transportinglayer. In some embodiments, an injection layer is present in someembodiments, no injection layer is present

Barrier Layer

A barrier layer is a layer capable of inhibiting charges (electrons orholes) and/or excitons present in the light-emitting layer from beingdiffused outside the light-emitting layer. In some embodiments, theelectron barrier layer is between the light-emitting layer and the holetransporting layer and inhibits electrons from passing through thelight-emitting layer toward the hole transporting layer. In someembodiments, the hole barrier layer is between the light-emitting layerand the electron transporting layer and inhibits holes from passingthrough the light-emitting layer toward the electron transporting layer.In some embodiments, the barrier layer inhibits excitons from beingdiffused outside the light-emitting layer. In some embodiments, theelectron barrier layer and the hole barrier layer are exciton barrierlayers. As used herein, the term “electron barrier layer” or “excitonbarrier layer” includes a layer that has the functions of both electronbarrier layer and of an exciton barrier layer.

Hole Barrier Layer

A hole barrier layer acts as an electron transporting layer. In someembodiments, the hole barrier layer inhibits holes from reaching theelectron transporting layer while transporting electrons. In someembodiments, the hole barrier layer enhances the recombinationprobability of electrons and holes in the light-emitting layer. Thematerial for the hole barrier layer may be the same materials as theones described for the electron transporting layer.

Electron Barrier Layer

As electron barrier layer transports holes. In some embodiments, theelectron barrier layer inhibits electrons from reaching the holetransporting layer while transporting holes. In some embodiments, theelectron barrier layer enhances the recombination probability ofelectrons and holes in the light-emitting layer.

Exciton Barrier Layer

An exciton barrier layer inhibits excitons generated throughrecombination of holes and electrons in the light-emitting layer frombeing diffused to the charge transporting layer. In some embodiments,the exciton barrier layer enables effective confinement of excitons inthe light-emitting layer. In some embodiments, the light emissionefficiency of the device is enhanced. In some embodiments, the excitonbarrier layer is adjacent to the light-emitting layer on any of the sideof the anode and the side of the cathode, and on both the sides. In someembodiments, where the exciton barrier layer is on the side of theanode, the layer can be between the hole transporting layer and thelight-emitting layer and adjacent to the light-emitting layer. In someembodiments, where the exciton barrier layer is on the side of thecathode, the layer can be between the light-emitting layer and thecathode and adjacent to the light-emitting layer. In some embodiments, ahole injection layer, an electron barrier layer, or a similar layer isbetween the anode and the exciton barrier layer that is adjacent to thelight-emitting layer on the side of the anode. In some embodiments, ahole injection layer, an electron barrier layer, a hole barrier layer,or a similar layer is between the cathode and the exciton barrier layerthat is adjacent to the light-emitting layer on the side of the cathode.In some embodiments, the exciton barrier layer comprises excited singletenergy and excited triplet energy, at least one of which is higher thanthe excited singlet energy and the excited triplet energy of thelight-emitting material, respectively.

Hole Transporting Layer

The hole transporting layer comprises a hole transporting material. Insome embodiments, the hole transporting layer is a single layer. In someembodiments, the hole transporting layer comprises a plurality oflayers.

In some embodiments, the hole transporting material has one of injectionor transporting property of holes and barrier property of electrons. Insome embodiments, the hole transporting material is an organic material.In some embodiments, the hole transporting material is an inorganicmaterial. Examples of known hole transporting materials that may be usedherein include but are not limited to a triazole derivative, anoxadiazole derivative, an imidazole derivative, a carbazole derivative,an indolocarbazole derivative, a polyarylalkane derivative, a pyrazolinederivative, a pyrazolone derivative, a phenylenediamine derivative, anarylamine derivative, an amino-substituted chalcone derivative, anoxazole derivative, a styrylanthracene derivative, a fluorenonederivative, a hydrazone derivative, a stilbene derivative, a silazanederivative, an aniline copolymer and an electroconductive polymeroligomer, particularly a thiophene oligomer, or a combination thereof.In some embodiments, the hole transporting material is selected from aporphyrin compound, an aromatic tertiary amine compound, and astyrylamine compound. In some embodiments, the hole transportingmaterial is an aromatic tertiary amine compound.

Electron-Transporting Layer

The electron-transporting layer comprises an electron transportingmaterial. In some embodiments, the electron-transporting layer is asingle layer. In some embodiments, the electron-transporting layercomprises a plurality of layer.

In some embodiments, the electron transporting material needs only tohave a function of transporting electrons, which are injected from thecathode, to the light-emitting layer. In some embodiments, the electrontransporting material also function as a hole barrier material. Examplesof the electron transporting layer that may be used herein include butare not limited to a nitro-substituted fluorene derivative, adiphenylquinone derivative, a thiopyran dioxide derivative,carbodiimide, a fluorenylidene methane derivative, anthraquinodimethane,an anthrone derivatives, an oxadiazole derivative, an azole derivative,an azine derivative, or a combination thereof, or a polymer thereof. Insome embodiments, the electron transporting material is a thiadiazolederivative, or a quinoxaline derivative. In some embodiments, theelectron transporting material is a polymer material.

In some embodiments, a compound of Formula (I) is comprised in thelight-emitting layer of a device of the invention. In some embodiments,a compound of Formula (I) is comprised in the light-emitting layer andat least one other layers. In some embodiments, the compounds of Formula(I) are independently selected for each layer. In some embodiments, thecompounds of Formula (I) are the same. In some embodiments, thecompounds of Formula (I) are different. For example, the compoundrepresented by Formula (I) may be used in the injection layer, thebarrier layer, the hole barrier layer, the electron barrier layer, theexciton barrier layer, the hole transporting layer, the electrontransporting layer and the like described above. The film forming methodof the layers are not particularly limited, and the layers may beproduced by any of a dry process and a wet process.

Specific examples of materials that can be used in the organicelectroluminescent device are shown below, but the materials that may beused in the invention are not construed as being limited to the examplecompounds. In some embodiments, a material having a particular functioncan also have another function.

In some embodiments, the host material is selected from the groupconsisting of:

Devices

In some embodiments, the compounds of the disclosure are incorporatedinto a device. For example, the device includes, but is not limited toan OLED bulb, an OLED lamp, a television screen, a computer monitor, amobile phone, and a tablet.

In some embodiments, an electronic device comprises an OLED comprisingan anode, a cathode, and at least one organic layer comprising alight-emitting layer between the anode and the cathode, wherein thelight-emitting layer comprises:

a host material; and

a compound of Formula (I).

In some embodiments, the light-emitting layer of the OLED furthercomprises a fluorescent material wherein the compound of Formula (I)converts triplets to singlets for the fluorescent emitter.

In some embodiments, compositions described herein may be incorporatedinto various light-sensitive or light-activated devices, such as OLEDsor photovoltaic devices. In some embodiments, the composition may beuseful in facilitating charge transfer or energy transfer within adevice and/or as a hole-transport material. The device may be, forexample, an organic light-emitting diode (OLED), an organic integratedcircuit (O-IC), an organic field-effect transistor (O-FET), an organicthin-film transistor (O-TFT), an organic light-emitting transistor(O-LET), an organic solar cell (O-SC), an organic optical detector, anorganic photoreceptor, an organic field-quench device (O-FQD), alight-emitting electrochemical cell (LEC) or an organic laser diode(O-laser).

Bulbs or Lamps

In some embodiments, an electronic device comprises: an OLED comprisingan anode, a cathode, and at least one organic layer; and an OLED drivercircuit, the organic layer comprising a light-emitting layer between theanode and the cathode, wherein the light-emitting layer comprises:

a host material; and

a compound of Formula (I),

wherein the compound of Formula (I) is a light emitting material.

In some embodiments, a device comprises OLEDs that differ in color. Insome embodiments, a device comprises an array comprising a combinationof OLEDs. In some embodiments, the combination of OLEDs is a combinationof three colors (e.g., RGB). In some embodiments, the combination ofOLEDs is a combination of colors that are not red, green, or blue (forexample, orange and yellow green). In some embodiments, the combinationof OLEDs is a combination of two, four, or more colors.

In some embodiments, a device is an OLED light comprising:

a circuit board having a first side with a mounting surface and anopposing second side, and defining at least one aperture;

at least one OLED on the mounting surface, the at least one OLEDconfigured to emanate light, comprising:

-   -   an anode, a cathode, and at least one organic layer comprising a        light-emitting layer between the anode and the cathode, wherein        the light-emitting layer comprises    -   a host material; and    -   a compound of Formula (I);    -   wherein the compound of Formula (I) is a light emitting        material;

a housing for the circuit board; and

at least one connector arranged at an end of the housing, the housingand the connector defining a package adapted for installation in a lightfixture.

In some embodiments, the OLED light comprises a plurality of OLEDsmounted on a circuit board such that light emanates in a plurality ofdirections. In some embodiments, a portion of the light emanated in afirst direction is deflected to emanate in a second direction. In someembodiments, a reflector is used to deflect the light emanated in afirst direction.

Displays or Screens

In some embodiments, the compounds of Formula (I) can be used in ascreen or a display. In some embodiments, the compounds of Formula (I)are deposited onto a substrate using a process including, but notlimited to, vacuum evaporation, deposition, vapor deposition, orchemical vapor deposition (CVD). In some embodiments, the substrate is aphotoplate structure useful in a two-sided etch provides a unique aspectratio pixel. The screen (which may also be referred to as a mask) isused in a process in the manufacturing of OLED displays. Thecorresponding artwork pattern design facilitates a very steep and narrowtie-bar between the pixels in the vertical direction and a large,sweeping bevel opening in the horizontal direction. This allows theclose patterning of pixels needed for high definition displays whileoptimizing the chemical deposition onto a TFT backplane.

The internal patterning of the pixel allows the construction of a3-dimensional pixel opening with varying aspect ratios in the horizontaland vertical directions. Additionally, the use of imaged “stripes” orhalftone circles within the pixel area inhibits etching in specificareas until these specific patterns are undercut and fall off thesubstrate. At that point the entire pixel area is subjected to a similaretch rate, but the depths are varying depending on the halftone pattern.Varying the size and spacing of the halftone pattern allows etching tobe inhibited at different rates within the pixel allowing for alocalized deeper etch needed to create steep vertical bevels.

A preferred material for the deposition mask is invar. Invar is a metalalloy that is cold rolled into long thin sheet in a steel mill. Invarcannot be electrodeposited onto a rotating mandrel as the nickel mask. Apreferred and more cost feasible method for forming the open areas inthe mask used for deposition is through a wet chemical etching.

In some embodiments, a screen or display pattern is a pixel matrix on asubstrate. In some embodiments, a screen or display pattern isfabricated using lithography (e.g., photolithography and e-beamlithography). In some embodiments, a screen or display pattern isfabricated using a wet chemical etch. In further embodiments, a screenor display pattern is fabricated using plasma etching.

Methods of Manufacturing Devices Using the Disclosed Compounds

An OLED display is generally manufactured by forming a large motherpanel and then cutting the mother panel in units of cell panels. Ingeneral, each of the cell panels on the mother panel is formed byforming a thin film transistor (TFT) including an active layer and asource/drain electrode on a base substrate, applying a planarizationfilm to the TFT, and sequentially forming a pixel electrode, alight-emitting layer, a counter electrode, and an encapsulation layer,and then is cut from the mother panel.

An OLED display is generally manufactured by forming a large motherpanel and then cutting the mother panel in units of cell panels. Ingeneral, each of the cell panels on the mother panel is formed byforming a thin film transistor (TFT) including an active layer and asource/drain electrode on a base substrate, applying a planarizationfilm to the TFT, and sequentially forming a pixel electrode, alight-emitting layer, a counter electrode, and an encapsulation layer,and then is cut from the mother panel.

In another aspect, provided herein is a method of manufacturing anorganic light-emitting diode (OLED) display, the method comprising:

forming a barrier layer on a base substrate of a mother panel;

forming a plurality of display units in units of cell panels on thebarrier layer;

forming an encapsulation layer on each of the display units of the cellpanels; and

applying an organic film to an interface portion between the cellpanels.

In some embodiments, the barrier layer is an inorganic film formed of,for example, SiNx, and an edge portion of the barrier layer is coveredwith an organic film formed of polyimide or acryl. In some embodiments,the organic film helps the mother panel to be softly cut in units of thecell panel.

In some embodiments, the thin film transistor (TFT) layer includes alight-emitting layer, a gate electrode, and a source/drain electrode.Each of the plurality of display units may include a thin filmtransistor (TFT) layer, a planarization film formed on the TFT layer,and a light-emitting unit formed on the planarization film, wherein theorganic film applied to the interface portion is formed of a samematerial as a material of the planarization film and is formed at a sametime as the planarization film is formed. In some embodiments, alight-emitting unit is connected to the TFT layer with a passivationlayer and a planarization film therebetween and an encapsulation layerthat covers and protects the light-emitting unit. In some embodiments ofthe method of manufacturing, the organic film contacts neither thedisplay units nor the encapsulation layer.

Each of the organic film and the planarization film may include any oneof polyimide and acryl. In some embodiments, the barrier layer may be aninorganic film. In some embodiments, the base substrate may be formed ofpolyimide. The method may further include, before the forming of thebarrier layer on one surface of the base substrate formed of polyimide,attaching a carrier substrate formed of a glass material to anothersurface of the base substrate, and before the cutting along theinterface portion, separating the carrier substrate from the basesubstrate. In some embodiments, the OLED display is a flexible display.

In some embodiments, the passivation layer is an organic film disposedon the TFT layer to cover the TFT layer. In some embodiments, theplanarization film is an organic film formed on the passivation layer.In some embodiments, the planarization film is formed of polyimide oracryl, like the organic film formed on the edge portion of the barrierlayer. In some embodiments, the planarization film and the organic filmare simultaneously formed when the OLED display is manufactured. In someembodiments, the organic film may be formed on the edge portion of thebarrier layer such that a portion of the organic film directly contactsthe base substrate and a remaining portion of the organic film contactsthe barrier layer while surrounding the edge portion of the barrierlayer.

In some embodiments, the light-emitting layer includes a pixelelectrode, a counter electrode, and an organic light-emitting layerdisposed between the pixel electrode and the counter electrode. In someembodiments, the pixel electrode is connected to the source/drainelectrode of the TFT layer.

In some embodiments, when a voltage is applied to the pixel electrodethrough the TFT layer, an appropriate voltage is formed between thepixel electrode and the counter electrode, and thus the organiclight-emitting layer emits light, thereby forming an image. Hereinafter,an image forming unit including the TFT layer and the light-emittingunit is referred to as a display unit.

In some embodiments, the encapsulation layer that covers the displayunit and prevents penetration of external moisture may be formed to havea thin film encapsulation structure in which an organic film and aninorganic film are alternately slacked. In some embodiments, theencapsulation layer has a thin film encapsulation structure in which aplurality of thin films are stacked. In some embodiments, the organicfilm applied to the interface portion is spaced apart from each of theplurality of display units. In some embodiments, the organic film isformed such that a portion of the organic film directly contacts thebase substrate and a remaining portion of the organic film contacts thebarrier layer while surrounding an edge portion of the barrier layer.

In one embodiment, the OLED display is flexible and uses the soft basesubstrate formed of polyimide. In some embodiments, the base substrateis formed on a carrier substrate formed of a glass material, and thenthe carrier substrate is separated.

In some embodiments, the barrier layer is formed on a surface of thebase substrate opposite to the carrier substrate. In one embodiment, thebarrier layer is patterned according to a size of each of the cellpanels. For example, while the base substrate is formed over the entiresurface of a mother panel, the barrier layer is formed according to asize of each of the cell panels, and thus a groove is formed at aninterface portion between the barrier layers of the cell panels. Each ofthe cell panels can be cut along the groove.

In some embodiments, the method of manufacture further comprises cuttingalong the interface portion, wherein a groove is formed in the barrierlayer, wherein at least a portion of the organic film is formed in thegroove, and wherein the groove does not penetrate into the basesubstrate. In some embodiments, the TFT layer of each of the cell panelsis formed, and the passivation layer which is an inorganic film and theplanarization film which is an organic film are disposed on the TFTlayer to cover the TFT layer. At the same time as the planarization filmformed of, for example, polyimide or acryl is formed, the groove at theinterface portion is covered with the organic film formed of, forexample, polyimide or acryl. This is to prevent cracks from occurring byallowing the organic film to absorb an impact generated when each of thecell panels is cut along the groove at the interface portion. That is,if the entire barrier layer is entirely exposed without the organicfilm, an impact generated when each of the cell panels is cut along thegroove at the interface portion is transferred to the barrier layer,thereby increasing the risk of cracks. However, in one embodiment, sincethe groove at the interface portion between the barrier layers iscovered with the organic film and the organic film absorbs an impactthat would otherwise be transferred to the barrier layer, each of thecell panels may be softly cut and cracks may be prevented from occurringin the barrier layer. In one embodiment, the organic film covering thegroove at the interface portion and the planarization film are spacedapart from each other. For example, if the organic film and theplanarization film are connected to each other as one layer, sinceexternal moisture may penetrate into the display unit through theplanarization film and a portion where the organic film remains, theorganic film and the planarization film are spaced apart from each othersuch that the organic film is spaced apart from the display unit.

In some embodiments, the display unit is formed by forming thelight-emitting unit, and the encapsulation layer is disposed on thedisplay unit to cover the display unit. As such, once the mother panelis completely manufactured, the carrier substrate that supports the basesubstrate is separated from the base substrate. In some embodiments,when a laser beam is emitted toward the carrier substrate, the carriersubstrate is separated from the base substrate due to a difference in athermal expansion coefficient between the carrier substrate and the basesubstrate.

In some embodiments, the mother panel is cut in units of the cellpanels. In some embodiments, the mother panel is cut along an interfaceportion between the cell panels by using a cutter. In some embodiments,since the groove at the interface portion along which the mother panelis cut is covered with the organic film, the organic film absorbs animpact during the cutting. In some embodiments, cracks may be preventedfrom occurring in the barrier layer during the cutting.

In some embodiments, the methods reduce a defect rate of a product andstabilize its quality.

Another aspect is an OLED display including: a barrier layer that isformed on a base substrate; a display unit that is formed on the barrierlayer; an encapsulation layer that is formed on the display unit; and anorganic film that is applied to an edge portion of the barrier layer.

All of the documents cited in this specification are expresslyincorporated by reference, in its entirety, into the presentapplication.

EXAMPLES

An embodiment of the present disclosure provides the preparation ofcompounds of Formula (I) according to the procedures of the followingexamples, using appropriate materials. Those skilled in the art willunderstand that known variations of the conditions and processes of thefollowing preparative procedures can be used to prepare these compounds.Moreover, by utilizing the procedures described in detail, one ofordinary skill in the art can prepare additional compounds of thepresent disclosure.

General Information on Analytical Methods

The features of the invention will be described more specifically withreference to examples below. The materials, processes, procedures andthe like shown below may be appropriately modified unless they deviatefrom the substance of the invention. Accordingly, the scope of theinvention is not construed as being limited to the specific examplesshown below. The characteristics of samples were evaluated by using NMR(Nuclear Magnetic Resonance 500 MHz, produced by Bruker), LC/MS (LiquidChromatography Mass Spectrometry, produced by Waters), AC3 (produced byRIKEN KEIKI), High-performance UV/Vis/NIR Spectrophotometer (Lambda 950,produced by PerkinElmer, Co., Ltd.), Fluorescence Spectrophotometer(FluoroMax-4, produced by Horiba, Ltd.), Photonic multichannel analyzer(PMA-12 C10027-01, produced by Hamamatsu Photonics K.K.), Absolute PLQuantum Yield Measurement System (C11347, produced by HamamatsuPhotonics K.K.), Automatic Current voltage brightness measurement system(ETS-170, produced by System engineers co ltd). Life Time MeasurementSystem (EAS-26C, produced by System engineers co ltd), and Streak Camera(Model C4334, produced by Hamamatsu Photonics K.K.).

Example 1

The principle of the features may be described as follows for an organicelectroluminescent device as an example.

In an organic electroluminescent device, carriers are injected from ananode and a cathode to a light-emitting material to form an excitedstate for the light-emitting material, with which light is emitted. Inthe case of a carrier injection type organic electroluminescent device,in general, excitons that are excited to the excited singlet state are25% of the total excitons generated, and the remaining 75% thereof areexcited to the excited triplet state. Accordingly, the use ofphosphorescence, which is light emission from the excited triplet state,provides a high energy utilization. However, the excited triplet statehas a long lifetime and thus causes saturation of the excited state anddeactivation of energy through mutual action with the excitons in theexcited triplet state, and therefore the quantum yield ofphosphorescence may generally be often not high. A delayed fluorescentmaterial emits fluorescent light through the mechanism that the energyof excitons transits to the excited triplet state through intersystemcrossing or the like, and then transits to the excited singlet statethrough reverse intersystem crossing due to triplet-triplet annihilationor absorption of thermal energy, thereby emitting fluorescent light. Itis considered that among the materials, a thermal activation typedelayed fluorescent material emitting light through absorption ofthermal energy is particularly useful for an organic electroluminescentdevice. In the case where a delayed fluorescent material is used in anorganic electroluminescent device, the excitons in the excited singletstate normally emit fluorescent light. On the other hand, the excitonsin the excited triplet state emit fluorescent light through intersystemcrossing to the excited singlet state by absorbing the heat generated bythe device. At this time, the light emitted through reverse intersystemcrossing from the excited triplet state to the excited singlet state hasthe same wavelength as fluorescent light since it is light emission fromthe excited singlet state, but has a longer lifetime (light emissionlifetime) than the normal fluorescent light and phosphorescent light,and thus the light is observed as fluorescent light that is delayed fromthe normal fluorescent light and phosphorescent light. The light may bedefined as delayed fluorescent light. The use of the thermal activationtype exciton transition mechanism may raise the proportion of thecompound in the excited singlet state, which is generally formed in aproportion only of 25%, to 25% or more through the absorption of thethermal energy after the carrier injection. A compound that emits strongfluorescent light and delayed fluorescent light at a low temperature oflower than 100° C. undergoes the intersystem crossing from the excitedtriplet state to the excited singlet state sufficiently with the heat ofthe device, thereby emitting delayed fluorescent light, and thus the useof the compound may drastically enhance the light emission efficiency.

Example 2

The compounds of the invention can be synthesized by any method known toone of ordinary skills in the art. The compounds are synthesized fromthe commonly available starting material. The various moieties can beassembled via linear or branched synthetic routes.

Synthesis of Compound 53

A mixture of 9H-carbazole (1a, 3.3 g, 20 mmol) and potassium carbonate(5.8 g, 10.5 mmol) in DMF (240 mL) solution was stirred at 60° C. undernitrogen atmosphere for 30 min. 4-bromotetrafluoropyridine (2a, 0.92 g,4 mmol) was added to the solution. After stirring for 15 h, to thesolution was added water, and the resulting mixture was filtrated. Theobtained residue was purified by flash silica gel column chromatographyusing toluene as eluent to afford target material9,9′,9″,9′″-(4-bromopyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole) (3a,2.1 g, 2.6 mmol, 64%).

MS (ASAP): 821 (M+H⁺, cal. C₅₃H₃₂BrN₅, 821); ¹H NMR (500 MHz, CDCl₃):8.82 (s, 2H), 7.80 (s, 2H), 7.74-7.72 (m, 4H), 7.51-7.48 (m, 4H), 7.25(d, J=7.5 Hz, 4H), 7.21 (t, J=7.5 Hz, 4H), 7.14 (t, J=7.5 Hz, 4H),7.09-7.06 (m, 8H).

To a stirred solution of9,9′,9″,9′″-(4-bromopyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole) (3a,2.1 g, 2.6 mmol) and4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phthalonitrile (4a, 2.0g, 7.8 mmol) in toluene (300 mL) and water (100 mL) were addedPd(PPh₃)₂Cl₂ (182 mg, 0.26 mmol) and sodium carbonate (0.83 g, 7.8mmol). The solution was stirred in 100° C. for 15 h under nitrogenatmosphere. After cooling to room temperature, the resulting mixture wasconcentrated in vacuo and then purified by flash silica gel columnchromatography using gradient eluent of DCM/n-hexane mixture from 1:1 to2:1. The obtained solid was further purified from recrystallization toafford Compound 53 in 640 mg (0.74 mmol, 29%).

MS (ASAP): 867 (M+H³⁰, cal.: C₆₁H₃₅N₇, 867), ¹H NMR (500 MHz, CDCl₃):7.78 (d, J=8.0 Hz, 4H), 7.72 (d, J=8.0 Hz, 4H), 7.43 (br. d, 4H), 7.08(t, J=7.5 Hz, 4H), 7.02-6.97 (br., 8H), 6.98 (t, J=8.0 Hz, 4H),6.87-6.83 (m, 5H), 6.74 (d, J=8.0 Hz, 1H), 6.72 (s, 1H).

Synthesis of Compound 1

To a stirred solution of9,9′,9″,9′″-(4-bromopyridine-2,3,5,6-tetrayl)tetrakis(9H-carbazole) (2.1g, 2.6 mmol) and3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phthalonitrile (2.0 g,7.8 mmol) in toluene (300 mL) and water (100 mL) are added Pd(PPh₃)₂Cl₂(182 mg, 0.26 mmol) and sodium carbonate (0.83 g, 7.8 mmol). Thesolution is stirred at 100° C. for 15 h under nitrogen atmosphere. Aftercooling to room temperature, the resulting mixture is concentrated invacuo and then purified by flash silica gel column chromatography using1:1 (v/v) CH₂Cl₂/n-hexane as eluent to afford Compound 1.

Example 3

Compound 53 synthesised in Example 2 was vapor-deposited on a quartzsubstrate by a vacuum vapor deposition method under a condition of avacuum degree of 10⁻³ Pa or less, so as to form a thin film having athickness of 70 nm.

The sample was irradiated with light having a wavelength of 300 nm at300 K., and thus the light emission spectrum was measured and designatedas fluorescence. The time resolved spectrum was obtained by excitationlight 300 nm with Photonic multichannel analyzer. The result is shown inFIG. 2. Delayed fluorescent light was observed.

Example 4

Thin films were laminated on a glass substrate having formed thereon ananode formed of indium tin oxide (ITO) having a thickness of 100 nm, bya vacuum vapor deposition method at a vacuum degree of 1.0×10⁻⁴ Pa orless. Firstly, HAT-CN was formed to a thickness of 10 nm on ITO, andthereon TrisPCz was formed to a thickness of 25 nm. mCBP was formed to athickness of 5 nm, and thereon Compound 53 and mCBP were thenvapor-co-deposited from separate vapor deposition sources to form alayer having a thickness of 30 nm, which is designated as a lightemitting layer. At this time, the concentration of compound 53 was 20%by weight. SF3-TRZ was then formed to a thickness of 10 nm, and thereonSF3-TRZ and Liq (7:3) were vapor-co-deposited to a thickness of 40 nm.Liq was then vacuum vapor-deposited to a thickness of 2 nm, and thenaluminum (Al) was vapor-deposited to a thickness of 100 nm to form acathode, thereby producing an organic electroluminescent device.

Comparative organic electroluminescent device was produced in the samemanner except that Comparative Compound 1 disclosed in OrganicElectronics 57 (2018) 247-254 was used instead of Compound 53.

External quantum efficiency (EQE) and time to reach 90% of initialluminance 3000 cd/m² (LT90) of the produced devices were measured. Theresults are shown in the following table. The device of the inventionhad high EQE and long lifetime.

Compound contained EQE LT90 in the light-emitting layer (%) (relativevalue) Compound 53 17.6 8 Comparative Compound 1 2.5 1

1. A compound of Formula (I):

wherein: two of Z¹, Z², Z³, Z⁴ and Z⁵ are independently A, the otherremaining three of Z¹, Z², Z³, Z⁴ and Z⁵ are independently selected fromH, deuterium, substituted or unsubstituted alkyl, and A, A is selectedfrom CN, substituted or unsubstituted aryl having at least one cyano,and substituted or unsubstituted heteroaryl having at least one nitrogenatom as a ring-constituting atom, two of R¹, R², R³ and R⁴ areindependently D, the other remaining two of R¹, R², R³ and R⁴ areselected from H, deuterium, substituted or unsubstituted alkyl,substituted or unsubstituted aryl, substituted or unsubstitutedheteroaryl, and D, D is group of Formula (IIa), (IIb), (IIc) or (IId):

R^(D) is independently selected from hydrogen, deuterium, substituted orunsubstituted alkyl, substituted or unsubstituted alkoxy, substituted orunsubstituted amino, substituted or unsubstituted aryl, substituted orunsubstituted aryloxy, substituted or unsubstituted heteroaryl,substituted or unsubstituted heteroaryloxy, and silyl; two or moreinstances of R^(D) taken together can form a ring system; R^(D′) isindependently selected from hydrogen, deuterium, substituted orunsubstituted alkyl, substituted or unsubstituted amino, substituted orunsubstituted aryl, and substituted or unsubstituted heteroaryl; two ormore instances of R^(D′) and R^(D) taken together can form a ringsystem; L^(D) is independently selected from single bond, substituted orunsubstituted arylene, and substituted or unsubstituted heteroarylene:wherein each instance of arylene and heteroarylene can be substitutedwith one or more substituents independently selected from deuterium,substituted or unsubstituted alkyl, substituted or unsubstituted aryl,and substituted or unsubstituted heteroaryl; two or more of thesesubstituents taken together can form a ring system; C—R^(D) of thebenzene rings in Formulae (IIa), (IIb), (IIc) and (IId) may besubstituted with N; and each “*” represents a point of attachment toFormula (I).
 2. The compound of claim 1, wherein two of Z¹, Z², Z³, Z⁴and Z⁵ are CN.
 3. The compound of claim 1, wherein Z¹ and Z² are A. 4.The compound of claim 1, wherein Z² and Z³ are A.
 5. The compound ofclaim 1, wherein the other remaining three of Z¹, Z², Z³, Z⁴ and Z⁵ areH.
 6. The compound of claim 1, wherein two of R¹, R², R³ and R⁴ areindependently group of Formula (IIa).
 7. The compound of claim 1,wherein two of R¹, R², R³ and R⁴ are independently group of Formula(IIb).
 8. The compound of claim 1, wherein at least one of the otherremaining two of R¹, R², R³ and R⁴ is substituted or unsubstituted aryl.9. The compound of claim 1, wherein at least one of the other remainingtwo of R¹, R², R³ and R⁴ is unsubstituted phenyl.
 10. The compound ofclaim 1, wherein three of R¹, R², R³ and R⁴ are independently D, and theremaining one of R¹, R², R³ and R⁴ is H, substituted or unsubstitutedalkyl, substituted or unsubstituted aryl, or substituted orunsubstituted heteroaryl.
 11. The compound of claim 1, wherein R¹, R²,R³ and R⁴ are independently D.
 12. The compound of claim 1, wherein bothof R¹ and R⁴ are not H. 13-16. (canceled)
 17. An organic light-emittingdiode (OLED) comprising the compound of claim
 1. 18. The organiclight-emitting diode (OLED) of claim 17, comprising an anode, a cathode,and at least one organic layer comprising a light-emitting layer betweenthe anode and the cathode, wherein the light-emitting layer comprises ahost material and the compound.
 19. The organic light-emitting diode(OLED) of claim 17, comprising an anode, a cathode, and at least oneorganic layer comprising a light-emitting layer between the anode andthe cathode, wherein the light-emitting layer comprises the compound anda light-emitting material, and light emission of the OLED occurs mainlyin the light-emitting material.
 20. The organic light-emitting diode(OLED) of claim 17, comprising an anode, a cathode, and at least oneorganic layer comprising a light-emitting layer between the anode andthe cathode, wherein the light-emitting layer comprises a host material,an assistant dopant and a light-emitting material, and the assistantdopant is the compound.